1H-Benzimidazole, 2-(chloromethyl)-1-ethyl- → tert-butyl (3RS,4RS,5SR)-4-(4-chloro-phenyl)-3-(1-ethyl-1H-benzimidazol-2-ylmethoxy)-5-propyl-piperidine-1-carboxylate

HRID 1858697Notes

Reaction equation

HRID 1858697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH:9]2[OH:24])=[CH:4][CH:3]=1.Cl[CH2:26][C:27]1[N:31]([CH2:32][CH3:33])[C:30]2[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=2[N:28]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:10][CH:9]2[O:24][CH2:26][C:27]2[N:31]([CH2:32][CH3:33])[C:30]3[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=3[N:28]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 124084321H-Benzimidazole, 2-(chloromethyl)-1-ethyl-HCID 86604427tert-butyl (3RS,4RS,5SR)-4-(4-chloro-phenyl)-3-hydroxy-5-propyl-piperidine-1-carboxylate

Product 1

HCID 86604429tert-butyl (3RS,4RS,5SR)-4-(4-chloro-phenyl)-3-(1-ethyl-1H-benzimidazol-2-ylmethoxy)-5-propyl-piperidine-1-carboxylate

Procedure

In an analogous manner to that described in Example 62(h), by alkylating tert-butyl (3RS,4RS,5SR)-4-(4-chloro-phenyl)-3-hydroxy-5-propyl-piperidine-1-carboxylate with 2-chloromethyl-1-ethyl-1H-benzoimidazole [Acta Pol. Pharm. 1977, 34(4), 359-369] there was obtained tert-butyl (3RS,4RS,5SR)-4-(4-chloro-phenyl)-3-(1-ethyl-1H-benzimidazol-2-ylmethoxy)-5-propyl-piperidine-1-carboxylate as a colourless oil, MS: 495 (M+H)+.

Sources & evidence

ORD record
ord-4b2500f0a1be40f0a4fc5a7e7d3f03be
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

Loading…