Diethyl Ether → HCID 23294462, compound

HRID 1955179Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 4-benzyl-1-(2-(4-nitrophenoxy)ethyl)piperidine hydrobromide (900 mg, 2.14 mmol) and Pd/C (10%; 100 mg) in MeOH (50 mL) was shaken under H2 (20-30 psi, Parr) for 2.25 h at 25° C. The catalyst was removed by filtration (Celite). The resulting solution was acidified with a dilute solution of HBr in MeOH. The MeOH was removed in vacuo (rotoevap) to give a syrup. Ether (45 mL) was added and the resulting mixture was vigorously stirred at 25° C. for 48 h. A gray suspension was obtained. The solid was collected, washed with ether (3×3 mL) and dried in vacuo (0.005 Torr, 56° C.) to give a beige powder (606 mg, 60%): mp>130° C.; 1H NMR (DMSO-d6) 1.33-1.88 (m, 5 H), 2.38-3.75 (m, 8 H), 4.25-4.45 (m, 2 H), 7.04-7.38 (m, 9 H), 9.49-10.30 (m, 4 H).

Workup

customThe catalyst was removed by filtration (Celite)
customThe MeOH was removed in vacuo (rotoevap)
customto give a syrup
stirringthe resulting mixture was vigorously stirred at 25° C. for 48 h
customA gray suspension was obtained
customThe solid was collected
washwashed with ether (3×3 mL)
customdried in vacuo (0.005 Torr, 56° C.)

Sources & evidence

ORD record: ord-47cf07e581f0426d9d6e452567287fcb
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124323

Reaction notes

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