HCID 178484001, compound → HCID 178484000, compound

HRID 1382939Notes

Reaction equation

HRID 1382939 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][N:18](C)[C:19](=O)OCC2C=CC=CC=2)[CH2:13][CH2:12]1>C(O)C.[Pd]>[CH3:19][NH:18][CH2:17][C@H:14]1[CH2:15][CH2:16][C@H:11]([C:3]2[N:2]([CH3:1])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N:4]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 178484001HCID 178484001, compound

Product 1

HCID 178484000HCID 178484000, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.9 g of benzyl [[trans-4-(1-methyl-2-benzimidazolyl)cyclohexyl]methyl]methylcarbamate are dissolved in 600 ml of ethanol and hydrogenated at room temperature and normal pressure after the addition of 1 g of 5% palladium-on-active charcoal. The product. isolated in the usual manner, is chromatographed on 250 g of silica gel firstly with methylene chloride/methanol (1:1) and then with methanol/concentrated ammonium hydroxide (100:1) as the elution agent. There are obtained 3.3 g (85%) of 2-[trans-4-[(methylamino)methyl]cyclohexyl]-1-methyl-benzimidazole as a thick oil.

Workup

  1. customisolated in the usual manner
  2. customis chromatographed on 250 g of silica gel firstly with methylene chloride/methanol (1:1)

Sources & evidence

ORD record
ord-ce510b4da8d14c7bb0013cdeb117558c
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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