tert-Butyl 4-(4-nitrophenyl)-1,4-diazepane-1-carboxylate → Tert-butyl 4-(4-aminophenyl)-1,4-diazepane-1-carboxylate

HRID 987508Notes

Reaction equation

HRID 987508 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CO.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([N:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 18008978tert-Butyl 4-(4-nitrophenyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 18008968Tert-butyl 4-(4-aminophenyl)-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Boc-4-(4-nitrophenyl)homopiperazine (prepared with 1-fluoro-4-nitrobenzene, 1-Boc-homopiperazine, Cs2CO3 in heated DMF) was dissolved in methanol. To it was added 10% Pd/C. The slurry was stirred under a hydrogen balloon for 2 hrs. It was filtered through celite and evaporated in vacuuo to give 1-(4-aminophenyl)-4-Boc-homopiperazine. ES-MS: (M+H)+292.

Workup

  1. filtrationIt was filtered through celite
  2. customevaporated in vacuuo

Sources & evidence

ORD record
ord-41465f5e931641b6b84f6b9c4761113b
Source dataset
uspto-grants-2003_10
Patent number
US06632815B2

Reaction notes

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