2-Chlorobenzimidazole → tert-Butyl 2-(((1H-benzo[d]imidazol-2-yl)amino)methyl)piperidine-1-carboxylate

HRID 18074

Reaction equation

HRID 18074 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:17]1[NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 71631700tert-Butyl 2-(((1H-benzo[d]imidazol-2-yl)amino)methyl)piperidine-1-carboxylateYield 30.8%

Conditions

Temperature
100 °C

Procedure

(RS)-2-Aminomethyl-piperidine-1-carboxylic acid tert butyl ester (0.25 g) and 2-chlorobenzimidazole (0.15 g) were combined and warmed to 100° C. for 48 hours. After cooling to room temperature the mixture was column chromatographed (silica gel, ethyl acetate/pentane 1:4-ethyl acetate/pentane 1:1 eluant) to give the title compound (0.1 g).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customchromatographed (silica gel, ethyl acetate/pentane 1:4-ethyl acetate/pentane 1:1 eluant)

Sources & evidence

ORD record
ord-cefcc925e2ad409b8db8b21058d013d6
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Linked notes

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