Method for preparing substituted 4-aminoindane derivatives

Patent metadata

Field	Value
Publication number	US-11180441-B2
Application number	US-201816624183-A
Country	US
Kind code	B2
Filing date	Jun 20, 2018
Priority date	Jun 27, 2017
Publication date	Nov 23, 2021
Grant date	Nov 23, 2021

Abstract

The present invention relates to a method for preparing substituted 4-aminoindane derivatives of the general formula (I)

by rearrangement of compounds of the formula (II) in HF, wherein R 1 , R 2 , R 3 , R 4 , and R 5 have the definitions as specified in the description.

First claim

The invention claimed is:

1. A process for preparing substituted 4-aminoindane derivative of general formula (I)

in which
R 1 is hydrogen, (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl,
R 2 , R 3 each are mutually independently hydrogen, (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl,
R 4 is CO—(C 1 -C 4 )-alkyl,
R 5 is hydrogen, halogen or (C 1 -C 4 )-alkyl,
comprising reacting a compound of Formula (II)

with anhydrous hydrogen fluoride.

2. The process according to claim 1 , wherein
R 1 is hydrogen or (C 1 -C 4 )-alkyl
R 2 and R 3 each are mutually independently hydrogen or (C 1 -C 4 )-alkyl,
R 4 is CO—(C 1 -C 4 -alkyl),
R 5 is hydrogen or (C 1 -C 4 )-alkyl.

3. The process according to claim 1 , wherein
R 1 is hydrogen, methyl, ethyl, n-propyl, isopropyl or n-butyl,
R 2 and R 3 each are mutually independently methyl, ethyl, n-propyl, isopropyl or n-butyl,
R 4 is CO—CH 3 ,
R 5 is hydrogen or methyl.

4. The process according to claim 1 , wherein
R 1 , R 2 and R 3 each are methyl,
R 4 is CO—CH 3 ,
R 5 is hydrogen.

5. The process according to claim 1 , wherein the process is carried out at a temperature in a range of from 0° C. and 50° C.

6. The process according to claim 1 , wherein the process is carried out at a temperature in a range of from 0° C. and 40° C.

7. The process according to claim 1 , wherein the process is carried out at a temperature in a range of from 0° C. and 30° C.

8. The process according to claim 1 , wherein the process is carried out at a temperature in a range of from 10° C. and 20° C.

9. The process according to claim 1 , wherein an amount of used hydrogen fluoride is in the range of 1 to 100 molar equivalents based on the total amount of compound of formula (II).

10. The process according to claim 1 , wherein reaction time of hydrogen fluoride with compounds of formula (II) is between 1 and 24 hours.

11. A process for preparation of a compound of formula (III)

wherein
R 1 is hydrogen, (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl,
R 2 , R 3 each are mutually independently hydrogen, (C 1 -C 8 )-alkyl or (C 3 -C 8 )-cycloalkyl,
R 4 is CO—(C 1 -C 4 )-alkyl,
R 5 is hydrogen, halogen or (C 1 -C 4 )-alkyl,

comprising the process according to claim 1 and further comprising hydrolyzing the compound of formula (I) in water to obtain the compound of formula (III).

12. The process according to claim 11 , wherein the process is carried out at a temperature in a range of from 50° C. to 100° C.

13. The process according to claim 1 , wherein an amount of used hydrogen fluoride is in a range of 5 to 30 molar equivalents based on the total amount of compound of formula (II).

14. The process according to claim 1 , wherein an amount of used hydrogen fluoride is in a range of 5 to 20 molar equivalents based on the total amount of compound of formula (II).

15. The process according to claim 1 , wherein a reaction time of hydrogen fluoride with compounds of formula (II) is between 10 and 22 hours.

Assignees

• Bayer Ag

Inventors

• Pazenok Sergii
• Saemann Christoph
• Shermolovich Yuriy

Classifications

• C07C231/12 Primary

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

• C07C211/60

  containing a ring other than a six-membered aromatic ring forming part of at least one of the condensed ring systems · CPC title

• C07C209/62 Primary

  by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds (C07C209/24 takes precedence) · CPC title

• C07C209/54 Primary

  by rearrangement reactions · CPC title