Ammonium formate → 6-Benzyl-1,4-diazepan-6-ylamine

HRID 424296Notes

Reaction equation

HRID 424296 reaction equation
C([N:8]1[CH2:14][C:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([N+:15]([O-])=O)[CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:18]([C:13]1([NH2:15])[CH2:14][NH:8][CH2:9][CH2:10][NH:11][CH2:12]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 585998471,4-Dibenzyl-6-benzyl-6-nitro-1,4-diazepane

Product 1

HCID 593813086-Benzyl-1,4-diazepan-6-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Pd—C 10% was added to a solution of 5 (200 mg, 0.27 mmol) and ammonium formate (0.75 g, 12.0 mmol) in methanol (10.0 mL) and the mixture was stirred at 60° C. for 1 h. The catalyst was removed and the methanolic solution was concentrated to give the amine 6 as an oil, which was dried under vacuum to give a foamy solid. Yield: 95 mg (92%).

Workup

  1. customThe catalyst was removed
  2. concentrationthe methanolic solution was concentrated

Sources & evidence

ORD record
ord-1224163f7a3c489393c3be46f696d5a4
Source dataset
uspto-grants-2012_01
Patent number
US08105567B2

Reaction notes

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