HCID 15485436, compound → HCID 15485445, compound

HRID 1955044Notes

Reaction equation

HRID 1955044 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[N+:24]([O-])=O>CCO.[Ni]>[CH2:15]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][N:9]1[CH2:8][CH2:7][O:6][C:5]1[CH:22]=[CH:23][C:2]([NH2:1])=[C:3]([NH2:24])[CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 15485436HCID 15485436, compound

Product 1

HCID 15485445HCID 15485445, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of of 1-[2-(4-amino-3-nitrophenoxy)ethyl]-2-benzylpiperidine (705 mg, 1.99 mmol) and Raney Ni (about 200 mg) in EtOH (15 mL) was shaken under H2 (35-25 parr) for 4 h, then filtered. The filtrate was evapoated, and the residure was purified by chromatography over silica gel (CHCl3 --MeOH, 3:2) to give 2-benzyl-1-[(3,4-diaminophenoxy)ethyl]piperidine (650 mg, 98%) as a brown viscous oil. 1H NMR (CDCl3): 1.22-1.32 (m, 2H), 1.49-1.52 (m, 3H), 2.49-2.56 (m, 2H), 2.756 (bs, 2H, NH2), 2.96-3.06 (m, 2H), 3.13-3.24 (m, 2H), 3.520 (bs, 2H, NH2), 4.02-4.12 (m, 2H), 6.285 (dd, 1H, J=9; 3), 6.350 (d, 1H, J=3), 6.640 (d, 1H, J=9), 7.16-7.30 (m, 5H).

Workup

  1. filtrationfiltered
  2. customthe residure was purified by chromatography over silica gel (CHCl3 --MeOH, 3:2)

Sources & evidence

ORD record
ord-981fd027996a4006bc301e1a17894d91
Source dataset
uspto-grants-2000_09
Patent number
US06124317

Reaction notes

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