[1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone → [1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone

HRID 555298Notes

Reaction equation

HRID 555298 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:17]3[CH:26]4[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:20][CH2:19][CH2:18]3)=[O:16])=[CH:14][C:9]=2[N:8]=[CH:7]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:17]3[CH:26]4[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:20][CH2:19][CH2:18]3)=[O:16])=[CH:14][C:9]=2[N:8]=[CH:7]1

Participants

4

Reactant 1

HCID 86630061[1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone

Product 1

HCID 66987299[1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanoneYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone (1.8 g, 0.0051 mol) in methanol (10 mL) was added 10% Pd/C (0.2 g). The reaction mixture was hydrogenated at 3 kg pressure for 2 h. The catalyst was filtered over celite and the filtrate was concentrated to give [1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone (1.5 g, 90%).

Workup

  1. filtrationThe catalyst was filtered over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4aa1b2c2b7594a91a66c6fbfb5f79fb7
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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