Granted Patent B2

US 10,570,105 · App. 16/408,216 · Granted Feb 25, 2020

Inventors: Catherine Tachdjian (San Diego, CA); Donald S. Karanewsky (Escondido, CA); Xiao-Qing Tang (Holmdel, NJ); Qing Chen (San Diego, CA); Peter Leeming (Monrovia, CA); Tayyab Rashid (Rancho Cucamonga, CA); Daniel Levin (La Canada, CA)

Assignee: Firmenich Incorporated

C07D285/16C01B21/096C07C231/02C07C231/14C07C235/20C07C237/44C07C253/30C07C255/54C07C255/57C07C255/59C07C303/40C07C307/10

Abstract

Claims (20)

1. A process of preparing a compound having structural formula (XI):

comprising:

reacting a compound having structural formula (XII):

with R 8 NH 2 under a pressure higher than the standard atmospheric pressure at a temperature ranging from about 90° C. to about 200° C.,

wherein

Y is C 1 -C 12 alkylene or C 1 -C 12 alkenylene;

R 8 is methyl, ethyl, propyl, butyl, pentyl, or hexyl; and

R 12 is C 1 -C 12 alkyl.

2. The process of claim 1 , wherein Y is selected from the group consisting of —CH 2 , —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —C(CH 3 ) 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 C(CH 3 ) 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 C(CH 3 ) 2 CH 2 —, —C(CH 3 ) 2 CH 2 CH 2 —, —CH 2 CH 2 C(CH 3 ) 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 C(CH 3 ) 2 CH 2 CH 2 —, —CH 2 CH 2 C(CH 3 ) 2 CH 2 —, —CH 2 CH 2 CH 2 C(CH 3 ) 2 —, and —CH 2 CH(CH 2 CH 3 )CH 2 CH 2 —.

3. The process of claim 2 , wherein Y is —CH 2 C(CH 3 ) 2 —.

4. The process of claim 1 , wherein the compound having structural formula (XI) is

5. The process of claim 1 , wherein said reacting is conducted at a temperature ranging from about 100° C. to about 150° C.

6. The process of claim 5 , wherein said reacting is conducted at a temperature of about 120° C.

7. The process of claim 1 , wherein said reacting is conducted in a sealed reactor at a temperature of about 120° C.

8. The process of claim 1 , wherein the pressure ranges from greater than the standard atmospheric pressure to about 600 psig.

9. The process of claim 8 , wherein the pressure ranges from greater than the standard atmospheric pressure to about 500 psig.

10. The process of claim 9 , wherein the pressure ranges from greater than the standard atmospheric pressure to about 400 psig or below.

11. The process of claim 1 , wherein the molar ratio of R 8 NH 2 to the compound having structural formula (XI) is from about 1:1 to about 2:1.

12. The process of claim 11 , wherein the molar ratio of R 8 NH 2 to the compound having structural formula (XI) is from about 1.2:1 to about 1.8:1.

13. The process of claim 12 , wherein the molar ratio of R 8 NH 2 to the compound having structural formula (XI) is about 1.5:1.

Assignments (2)

Continuity (8)