Process for producing substituted amino alcohols

Patent metadata

Field	Value
Publication number	US-11453645-B2
Application number	US-201917291390-A
Country	US
Kind code	B2
Filing date	Oct 29, 2019
Priority date	Nov 9, 2018
Publication date	Sep 27, 2022
Grant date	Sep 27, 2022

Abstract

A process for producing a compound of the formula (I)

involves at least reacting a compound of the formula (II)

with hydrogen and water in the presence of at least one homogeneous transition metal catalyst TMC 1.

First claim

The invention claimed is:

1. A process for producing a compound of the formula (I)

wherein in the formula (I)
R 1 is hydrogen or an organic radical having from 1 to 40 carbon atoms,
R 2 is an organic radical having from 1 to 40 carbon atoms,
or R 1 and R 2 together with the atoms connecting them, form a divalent organic group having from 1 to 40 carbon atoms,

the process comprising:
reacting a compound of the formula (II)

wherein in the formula (II)
R 1 and R 2 have the same meaning as in formula (I), and
R 3 is hydrogen or an organic radical having from 1 to 40 carbon atoms,

with hydrogen and water in the presence of an ether solvent and at least one homogeneous transition metal catalyst (TMC 1) selected from [Ru(PPh 3 ) 3 (CO)(H)Cl],
in a molar ratio of water to ether solvent of 2:1 to 1:50.

2. The process according to claim 1 , wherein R 3 is hydrogen.

3. The process according to claim 1 , wherein the at least one homogeneous TMC 1 is [Ru(PPh 3 ) 3 (CO)(H)Cl] in combination with 1,1,1-tris(diphenylphosphinomethyl)ethane (Triphos) or bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos).

4. The process according to claim 1 , wherein the at least one homogeneous TMC 1 is used in an amount of 0.001 mol % to 20 mol %, calculated as transition metal and based on the amount of the compound of the formula (II) used in the process.

5. The process according to claim 1 , wherein the reaction between the compound of the formula (II), water, and hydrogen is performed at a pressure in the range from 10 to 180 bar.

6. The process according to claim 1 , wherein the reaction between the compound of the formula (II), water, and hydrogen is performed at a temperature in the range from 50° C. to 180° C.

7. The process according to claim 1 , wherein the at least one homogeneous TMC 1 is recycled by removing the compound of the formula (II) and other volatile compounds of a reaction mixture obtained after the reaction between the compound of the formula (II), water, and hydrogen, via distillation.

8. The process according to claim 1 , wherein the reaction between the compound of the formula (II), water, and hydrogen is carried out at different H 2 pressures,
wherein a lower H 2 pressure in the range from 1 to 80 bar is used at first to reduce the nitrile group of the compound of the formula (II), and afterwards H 2 pressure is increased to a pressure in the range from 90 to 200 bar to reduce the amide group of the compound of the formula (II).

Assignees

• Basf Se

Inventors

• Schaub Thomas
• Ernst Martin
• Calleja Pilar
• Hashmi A Stephen K

Classifications

• C07C231/22

  Separation; Purification; Stabilisation; Use of additives (separation of optical isomers C07C231/20) · CPC title

• C07C231/12 Primary

  by reactions not involving the formation of carboxamide groups · CPC title

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title

• C07C213/00

  Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton · CPC title

• C07C213/10

  Separation; Purification; Stabilisation; Use of additives · CPC title