IP Library › Granted Patent US 7,202,386
Granted Patent B2
US 7,202,386 · App. 10/644,500 · Granted Apr 10, 2007

Method for the preparation of sevoflurane

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Quick Facts
Patent No.
US 7,202,386
App. No.
10/644,500
Granted
Apr 10, 2007
Kind
B2
Abstract

A method for the preparation of sevoflurane which comprises (a) providing a liquid mixture of (CF 3 ) 2 CHOCH 2 Cl, hydrogen fluoride, and an amine and (b) reacting the mixture, to form (CF 3 ) 2 CHOCH 2 F.

Claims (22)

1. A method for the preparation of sevoflurane which comprises:

(a) providing a liquid mixture of (CF 3 ) 2 CHOCH 2 Cl, hydrogen flouride, and an amine; and

(b) reacting the mixture to form (CF 3 ) 2 CHOCH 2 F.

2. The method of claim 1 , wherein the mixture is reacted by heating.

3. The method of claim 1 , wherein the mixture is reacted by heating at 40° C. to 80° C.

4. The method of claim 1 , wherein the mixture is reacted by heating at 55° C. to 65° C.

5. The method of claim 1 , wherein the amine is selected from a primary amine, a secondary amine, or a tertiary amine.

6. The method of claim 5 , wherein the amine is selected from propylamine or diethylamine.

7. The method of claim 5 , wherein the amine is a tertiary amine.

8. The method of claim 7 , wherein the tertiary amine is a trialkylamine.

9. The method of claim 8 , wherein the trialkylamine is selected from triethylamine, tripropylamine, triisopropylamine, tributylamine, dimethyl ethyl amine, di-isopropyl ethyl amine, or mixtures thereof.

10. The method of claim 1 , wherein the amine is a cyclic amine.

11. The method of claim 10 , wherein the cyclic amine is selected from pyrrolidine, N-methyl pyrrolidine, or piperidine.

12. The method of claim 1 , wherein the mixture comprises (CF 3 ) 2 CHOCHCl 2 .

13. The method of claim 12 , wherein the mixture comprises from 0.01 to 20 percent by weight of(CF 3 ) 2 CHOCHCl 2 .

14. The method of claim 1 , wherein the mole ratio of the (CF 3 ) 2 CHOCH 2 Cl to the hydrogen flouride is from 1:1 to 1:2.

15. The method of claim 1 , wherein the mole ratio of the (CF 3 ) 2 CHOCH 2 Cl to the amine is from 1:0.3 to 1:2.

16. The method of claim 3 , wherein the mixture is reacted for 4 to 12 hours.

17. The method of claim 3 , wherein the mixture is reacted for 4 to 10 hours.

18. The method of claim 3 , wherein the mixture is reacted for 4 to 7 hours.

19. The method of claim 1 , wherein the yield of the reaction is at least 50 percent.

20. The method of claim 1 , wherein the yield of the reaction is at least 65 percent.

Assignments (17)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 6, 2016
From: HSBC BANK USA, NATIONAL ASSOCIATION
To: PIRAMAL CRITICAL CARE, INC.
Reel/Frame 038567/0736 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 10272794 PREVIOUSLY RECORDED AT REEL: 028427 FRAME: 0056. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE BY SECURED PARTY. Recorded Jul 10, 2015
From: CREDIT AGRICOLE CORPORATE AND INVESTMENT BANK, SINGAPORE
To: PIRAMAL CRITICAL CARE, INC.
Reel/Frame 036089/0033 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME OF THE ASSIGNEE PREVIOUSLY RECORDED AT REEL: 025599 FRAME: 0742. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 19, 2015
From: STANDARD CHARTERED BANK
To: PIRAMAL CRITICAL CARE, INC. AS SUCCESSOR BY MERGER TO MINRAD, INC.
Reel/Frame 036130/0555 →
RELEASE OF SECURITY INTEREST Recorded Jun 22, 2012
From: CREDIT AGRICOLE CORPORATE AND INVESTMENT BANK, SINGAPORE
To: PIRAMAL CRITICAL CARE, INC.
Reel/Frame 028427/0056 →
SECURITY INTEREST Recorded Jan 23, 2012
From: PIRAMAL CRITICAL CARE, INC.
To: CREDIT AGRICOLE CORPORATE AND INVESTMENT BANK SINGAPORE
Reel/Frame 027637/0840 →
SECURITY INTEREST Recorded Jun 13, 2011
From: PIRAMAL CRITICAL CARE, INC.
To: HSBC BANK USA, NATIONAL ASSOCIATION
Reel/Frame 026436/0740 →
RELEASE OF SECURITY INTEREST Recorded Dec 2, 2010
From: STANDARD CHARTERED BANK
To: PIRAMAL HEALTHCARE, INC., AS SUCCESSOR BY MERGER TO MINRAD, INC.
Reel/Frame 025599/0742 →
CHANGE OF NAME Recorded Feb 19, 2010
From: MINRAD INC.
To: PIRAMAL CRITICAL CARE, INC.
Reel/Frame 023963/0095 →
THIS IS A CORRECTIVE ASSIGNMENT FOR INTELLECTUAL SECURITY AGREEMENT DATED AS OF MARCH 23, 2009 BETWEEN MINRAD INC. AS GRANTOR AND STANDARD CHARTERED BANK AS SECURITY TRUSTEE FILED IN REEL 022440 AND FRAME 0478 ON MARCH 24, 2009. PATENT APPLICATION NUMBER 11/218,293 WAS INCORRECTLY ASSIGNED. THE CORRECT PATENT APPLICATION NUMBER SHOULD BE 11/281,293 Recorded Feb 10, 2010
From: MINRAD INC.
To: STANDARD CHARTERED BANK
Reel/Frame 023937/0402 →
SECURITY AGREEMENT Recorded Mar 24, 2009
From: MINRAD INC.
To: STANDARD CHARTERED BANK
Reel/Frame 022440/0478 →
RELEASE OF SECURITY INTEREST Recorded Dec 16, 2008
From: FIRST NIAGARA BANK
To: MINRAD INC.
Reel/Frame 021985/0117 →
TERMINATION OF SECURITY INTEREST IN PATENTS Recorded May 23, 2008
From: LAMINAR DIRECT CAPITAL, L.P.
To: MINRAD INC.
Reel/Frame 020986/0543 →
NOTICE OF GRANT OF SECURITY INTEREST Recorded Feb 25, 2008
From: MINRAD INC.
To: LAMINAR DIRECT CAPITAL L.P., AS AGENT
Reel/Frame 020550/0950 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE FROM ASSIGNMENT TO SECURITY AGREEMENT, PREVIOUSLY RECORDED ON REEL 019605 FRAME 0862. ASSIGNOR(S) HEREBY CONFIRMS THE COLLATERAL ASSIGNMENT OF PATENTS. Recorded Aug 8, 2007
From: MINRAD INC.
To: FIRST NIAGARA BANK
Reel/Frame 019658/0648 →
RELEASE OF SECURITY INTEREST Recorded Aug 7, 2007
From: KEYBANK NATIONAL ASSOCIATION
To: MINRAD INC.
Reel/Frame 019649/0924 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2007
From: MINRAD INC.
To: FIRST NIAGARA BANK
Reel/Frame 019605/0862 →
SECURITY AGREEMENT Recorded Dec 27, 2005
From: MINRAD, INC.
To: KEYBANK NATIONAL ASSOCIATION
Reel/Frame 016937/0497 →