Diethyl Ether → 1-(2-(4-Aminophenoxy)ethyl)-2-benzylpiperidine Dihydrobromide

HRID 1861750Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine hydrobromide (500 mg, 1.19 mmol) and Pd/C (10%, 50 mg, Aldrich) in MeOH (25 mL) was shaken under H2 (20-30 psi, Parr) for 2 h at 25° C. The catalyst was removed by filtration (Celite). The resulting solution was acidified with a dilute solution of HBr in MeOH (pH paper to red). The MeOH was removed in vacuo (rotoevaporator, 35-40° C.) to give a syrup. Ether (45 mL) was added and the resulting mixture was vigorously stirred at 25° C. for 24 h. A yellow suspension was obtained. The solid was collected, washed with ether (3×2 mL) and dried in vacuo (0.005 Torr, 56° C.) to give a beige powder (358 mg, 64%): mp 130° C.; 1H NMR (DMSO-d6) 1.28-1.95 (m, 6H), 2.69-3.95 (m, 7H), 4.60-4.55 (m, 2H), 7.08-7.42 (m, 9H), 9.60-10.25 (m, 4H); HRMS Calcd for C20H26N20: 310.2045. Found: 310.2040.

Workup

customThe catalyst was removed by filtration (Celite)
customThe MeOH was removed in vacuo (rotoevaporator, 35-40° C.)
customto give a syrup
stirringthe resulting mixture was vigorously stirred at 25° C. for 24 h
customA yellow suspension was obtained
customThe solid was collected
washwashed with ether (3×2 mL)
customdried in vacuo (0.005 Torr, 56° C.)

Sources & evidence

ORD record: ord-b99f7ebbe4094123a1b98bc68ba9f996
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06534525B1

Reaction notes

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