tert-Butyl 4-{[2-(2-nitrophenyl)ethyl]amino}piperidine-1-carboxylate → Tert-butyl 4-{[2-(2-aminophenyl)ethyl]amino}piperidine-1-carboxylate

HRID 1172289Notes

Reaction equation

HRID 1172289 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][CH2:7][NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 18444265tert-Butyl 4-{[2-(2-nitrophenyl)ethyl]amino}piperidine-1-carboxylate

Product 1

HCID 18444264Tert-butyl 4-{[2-(2-aminophenyl)ethyl]amino}piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-(2-nitrophenethylamino)piperidine-1-carboxylate (10.5 g) in EtOH (180 ml) was added 10% Pd/C (1.05 g) and the reaction mixture was stirred at RT under an atmosphere of H2 overnight. The reaction mixture was filtered and the resulting solution was evaporated to dryness giving the desired product (9.6 g). LC/MS (10% to 99%): M/Z (M+H)+ (obs)=320; tR=2.06.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe resulting solution was evaporated to dryness

Sources & evidence

ORD record
ord-4acb313dfdc043ffb17cd0ee9dd833dc
Source dataset
uspto-grants-2010_11
Patent number
US07834000B2

Reaction notes

Loading…