4-Benzyl-1-(2-(4-benzyloxy-3-nitrophenoxy)ethyl)piperidine → 1-(2-(3-Amino-4-hydroxyphenoxy)ethyl)-4-benzylpiperidine

HRID 1955238Notes

Reaction equation

HRID 1955238 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23]CC3C=CC=CC=3)=[C:19]([N+:31]([O-])=O)[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[NH2:31][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[OH:23])[O:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1

Participants

3

Reactant 1

HCID 232944524-Benzyl-1-(2-(4-benzyloxy-3-nitrophenoxy)ethyl)piperidine

Product 1

HCID 232945201-(2-(3-Amino-4-hydroxyphenoxy)ethyl)-4-benzylpiperidineYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-benzyl-1-(2-(4-benzyloxy-3-nitrophenoxy)ethyl)piperidine (1.40 g, 3.1 mmol) and 10% pd/C (about 500 mg) in MeOH (30 mL) was hydrogenated to give 1.0 g (98%) of 1-(2-(3-amino-4-hydroxyphenoxy)ethyl)-4-benzylpiperidine as a viscous oil. 1H NMR (CDCl3): 1.40-1.68 (m, 5H), 2.06-2.13 (m, 2H), 2.530 (t, 2H, J=5.5), 6.000 (d, 2H, J=8), 6.242 (bs, 1H), 6.534 (d, 1H, J=8), 7.12-7.19 (m, 5H).

Sources & evidence

ORD record
ord-094e067d2ed44121b1fcf3f6e8b5bb35
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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