IP Library Granted Patent US 7,705,184
Granted Patent B2
US 7,705,184 · App. 12/466,457 · Granted Apr 27, 2010

Method of making amphetamine

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Quick Facts
Patent No.
US 7,705,184
App. No.
12/466,457
Granted
Apr 27, 2010
Kind
B2
Abstract

A method in which a crude chlorinated product of a phenylpropanolamine, preferably prepared by reacting thionyl chloride with the phenylpropanolamine, is purified by contacting an aqueous solution of the crude product with carbon. The carbon-treated solution of the crude chlorinated product of a phenylpropanolamine is catalytically hydrogenated to the corresponding amphetamine derivative.

Claims (18)

1. A method for making amphetamine-related products of formula (I):

where R 1 is hydrogen or a lower alkyl group, and R 2 and R 3 are independently selected from hydrogen, halogen, lower alkyl groups, lower alkoxy groups, lower alkyl groups substituted with 1 to 5 halogens, lower alkoxy groups substituted with 1 to 5 halogens, or both R 2 and R 3 , when on adjacent carbons, together constitute —O(CH 2 ) x O— where x is an integer of 1 to 4, thereby forming a ring structure fused with the phenyl group, the method comprising:

dissolving a crude chlorinated phenylpropanolamine hydrochloride product of formula (II):

where R 1 , R 2 and R 3 have the same meanings as identified above in connection with formula (I), in water to form an aqueous solution, contacting the aqueous solution with carbon, and hydrogenating the carbon-treated aqueous solution.

2. The method of claim 1 wherein the crude chlorinated phenylpropanolamine hydrochloride product of formula (II) is prepared from a phenylpropanolamine.

3. The method of claim 1 wherein the crude chlorinated phenylpropanolamine hydrochloride product of formula (II) is prepared by adding thionyl chloride to a solution of a phenylpropanolamine in an organic solvent.

4. The method of claim 3 wherein the organic solvent is toluene.

5. The method of claim 2 wherein the crude chlorinated phenylpropanolamine hydrochloride product of formula (II) is prepared by adding thionyl chloride to a solution of a phenylpropanolamine in an organic solvent.

6. The method of claim 5 wherein the phenylpropanolamine is norephedrine.

7. The method of claim 6 wherein the organic solvent is toluene.

8. The method of claim 3 wherein the phenylpropanolamine is norephedrine.

9. The method of claim 2 wherein the phenylpropanolamine is norephedrine.

10. The method of claim 6 wherein the norephedrine is selected from the group consisting of l-norephedrine, d-norephedrine and d,l-norephedrine.

11. The method of claim 8 wherein the norephedrine is selected from the group consisting of l-norephedrine, d-norephedrine and d,l-norephedrine.

12. The method of claim 9 wherein the norephedrine is selected from the group consisting of l-norephedrine, d-norephedrine and d,l-norephedrine.

13. The method of claim 6 wherein the norephedrine is l-norephedrine.

14. The method of claim 8 wherein the norephedrine is l-norephedrine.

15. The method of claim 9 wherein the norephedrine is l-norephedrine.

Assignments (8)
ASSIGNMENT AND ASSUMPTION OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Apr 11, 2025
From: ARES AGENT SERVICES, L.P., AS FORMER AGENT
To: BLUE OWL CAPITAL CORPORATION, AS NEW AGENT
Reel/Frame 070821/0302 →
SECURITY INTEREST Recorded Mar 6, 2025
From: CAMBREX CHARLES CITY, INC.
To: ARES AGENT SERVICES, L.P., AS COLLATERAL AGENT
Reel/Frame 070421/0947 →
RELEASE OF FIRST LIEN SECURITY INTEREST IN PATENTS Recorded Mar 6, 2025
From: ROYAL BANK OF CANADA
To: CAMBREX CHARLES CITY, INC.; AVISTA PHARMA SOLUTIONS, INC.; SNAPDRAGON CHEMISTRY, INC.
Reel/Frame 070438/0333 →
RELEASE OF SECOND LIEN SECURITY INTEREST IN PATENTS Recorded Dec 7, 2020
From: ROYAL BANK OF CANADA, AS COLLATERAL AGENT
To: AVISTA PHARMA SOLUTIONS, INC.
Reel/Frame 054630/0307 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Dec 4, 2019
From: CAMBREX CHARLES CITY, INC.; AVISTA PHARMA SOLUTIONS, INC.
To: ROYAL BANK OF CANADA, AS COLLATERAL AGENT
Reel/Frame 051196/0080 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Dec 4, 2019
From: AVISTA PHARMA SOLUTIONS, INC.; CAMBREX CHARLES CITY, INC.
To: ROYAL BANK OF CANADA, AS COLLATERAL AGENT
Reel/Frame 051283/0877 →
NOTICE OF RELEASE OF SECURITY INTEREST IN PATENTS Recorded Dec 4, 2019
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: CAMBREX CHARLES CITY, INC.
Reel/Frame 051283/0903 →
SECURITY INTEREST Recorded Jan 3, 2019
From: CAMBREX CHARLES CITY, INC.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 047895/0053 →