HCID 23294453, compound → HCID 54139776, compound

HRID 1955229Notes

Reaction equation

HRID 1955229 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[CH:4][C:3]=1[N+:25]([O-])=O>CCO>[CH2:16]([CH:13]1[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][CH2:7][O:6][C:5]2[CH:23]=[CH:24][C:2]([NH2:1])=[C:3]([NH2:25])[CH:4]=2)[CH2:11][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 23294453HCID 23294453, compound

Product 1

HCID 54139776HCID 54139776, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

From a mixture of 1-[3-(4-Amino-3-nitrophenoxy)propyl]-4-benzylpiperidine (226 mg, 0.61 mmol) and stannous dihydrate (690 mg, 3.06 mmol) in EtOH (25 mL) was obtained 140 mg (67.6%) of 4-benzyl-1-[(3,4-diamino-phenoxy)propyl]piperidine as a yellowish viscous oil. 1H NMR (CDCl3): 1.24-1.37 (m, 2H), 1.46-1.58 (m, 1H), 1.58-1.70 (m, 2H), 1.81-1.97 (m, 4H), 2.458 (t, 2H, J=7.5), 2.536 (d, 2H, J=7), 2.90-2.93 (m, 2H), 3.063 (bs, 2H, NH2), 3.503 (bs, 2H, NH2), 3.904 (t, 2H, J=6.5), 6.250 (dd, 1H, J=8; 2.5), 6.319 (d, 1H, J=2.5), 6.619 (d, 1H, J=8), 7.13-7.30 (m, 5H).

Sources & evidence

ORD record
ord-14054f4862e7446195b1909f48616984
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

Loading…