1-Methyl-4-piperidyl benzilate → 4-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-([1,3,5]-triazin-2-ylcarbamoylmethyl)-piperidinium bromide

HRID 1690658Notes

Reaction equation

HRID 1690658 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9](=[O:24])[C:10]([OH:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.[Br:25][CH2:26][C:27]([NH:29][C:30]1[N:35]=[CH:34][N:33]=[CH:32][N:31]=1)=[O:28]>C(#N)C.C(Cl)(Cl)Cl>[Br-:25].[OH:23][C:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:9]([O:8][CH:5]1[CH2:6][CH2:7][N+:2]([CH3:1])([CH2:26][C:27](=[O:28])[NH:29][C:30]2[N:35]=[CH:34][N:33]=[CH:32][N:31]=2)[CH2:3][CH2:4]1)=[O:24]

Participants

4

Reactant 2

HCID 771571-Methyl-4-piperidyl benzilate2×HCID 669026202-Bromo-N-[1,3,5]triazin-2-yl-acetamide2×

Product 1

HCID 866342274-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-methyl-1-([1,3,5]-triazin-2-ylcarbamoylmethyl)-piperidinium bromide

Reagents, catalysts & solvents 1

HCID 22555007Acetonitrile chloroformSolvent

Procedure

A solution comprising hydroxy-diphenyl-acetic acid 1-methyl-piperidin-4-yl ester (Intermediate F) (0.3 g, 0.9 mmol) and 2-bromo-N-[1,3,5]triazin-2-yl-acetamide (Intermediate J) (0.2 g, 0.9 mmol) in acetonitrile/chloroform (2 ml of a 1:1 mixture) is stirred under an inert atmosphere of argon at room temperature for 2 days. The titled product is observed by LC-MS. (M+462.2)

Sources & evidence

ORD record
ord-feca80442ed64428b4aba2042068dd8b
Source dataset
uspto-grants-2012_04
Patent number
US08153669B2

Reaction notes

Loading…