Cyanogen Bromide → 1-Cyclohexyl-5-[(piperidin-1-yl)methyl]-1H-benzimidazol-2-amine

HRID 2068299Notes

Reaction equation

HRID 2068299 reaction equation
[CH:1]1([NH:7][C:8]2[C:9]([NH2:21])=[CH:10][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:22]#[C:23]Br>CO.C(#N)C.O>[CH:1]1([N:7]2[C:8]3[CH:13]=[CH:12][C:11]([CH2:14][N:15]4[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)=[CH:10][C:9]=3[N:21]=[C:23]2[NH2:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 10476Cyanogen BromideHCID 50989668N1-cyclohexyl-4-(piperidin-1-ylmethyl)benzene-1,2-diamine

Product 1

HCID 218991781-Cyclohexyl-5-[(piperidin-1-yl)methyl]-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

N1-cyclohexyl-4-(piperidin-1-ylmethyl)benzene-1,2-diamine from step3 in methanol (200 mL) was added to a mixture of 5 M cyanogen bromide in acetonitrile (3.2 mL) and water (100 mL) dropwise over 1 hr with stirring. After 4.5 hr total reaction time, the mixture was evaporated to dryness. The residue was purified by preparative HPLC chromatography to yield 2.23 g of the title compound as the bis-TFA salt.

Workup

  1. customthe mixture was evaporated to dryness
  2. customThe residue was purified by preparative HPLC chromatography

Sources & evidence

ORD record
ord-fd1d3aa6454e481f8c5422a7d4863ca8
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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