N,N,2,3-tetramethylbenzamide → (R)-3-[2-(3-hydroxypiperidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one

HRID 1159534Notes

Reaction equation

HRID 1159534 reaction equation
C[N:2]([CH3:13])[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH3:11].[OH:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][CH2:22]C#N)[CH2:16]1>>[OH:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][CH2:22][C:13]2[NH:2][C:3](=[O:12])[C:4]3[C:5]([CH:11]=2)=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=3)[CH2:16]1

Participants

3

Reactant 2

HCID 22931034N,N,2,3-tetramethylbenzamideHCID 68644317(R)-3-(3-hydroxypiperidin-1-yl)propionitrile

Product 1

HCID 11778762(R)-3-[2-(3-hydroxypiperidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-oneYield 6.5%

Procedure

By the reaction in the same manner as in Example 1a, using N,N-dimethyl-2,3-dimethylbenzamide (1.41 g) and (R)-3-(3-hydroxypiperidin-1-yl)propionitrile (1.44 g), (R)-3-[2-(3-hydroxypiperidin-1-yl)ethyl]-5-methyl-2H-isoquinolin-1-one (147 mg) was obtained.

Workup

  1. customBy the reaction in the same manner as in Example 1a

Sources & evidence

ORD record
ord-b6ae038f1bb342a997fab310562a7b99
Source dataset
uspto-grants-2010_10
Patent number
US07812178B2

Reaction notes

Loading…