Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(3-nitrobenzyloxy)piperidine-1-carboxylate → Tert-butyl 3-(3-aminobenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176392Notes

Reaction equation

HRID 1176392 reaction equation
[CH3:1][O:2][C:3]1[CH:44]=[CH:43][CH:42]=[CH:41][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([N+:38]([O-])=O)[CH:33]=2)=[CH:13][CH:12]=1>O1CCCC1.[Ni]>[NH2:38][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[CH2:31][O:30][CH:18]1[CH:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]3[CH:41]=[CH:42][CH:43]=[CH:44][C:3]=3[O:2][CH3:1])=[CH:16][CH:15]=2)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19]1

Participants

4

Reactant 1

HCID 68502850Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(3-nitrobenzyloxy)piperidine-1-carboxylate

Product 1

HCID 68505086Tert-butyl 3-(3-aminobenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The solution of 0.710 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(3-nitrobenzyloxy)piperidine-1-carboxylate in 10 ml of tetrahydrofuran is hydrogenated in the presence of 0.190 g of Raney nickel over 20 hours. The reaction mixture is filtered and the filtrate is concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.14 (1:2 EtOAc-heptane); Rt=4.93.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-050645de076944ed99e9d39cc7c98031
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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