Sodium Hydroxide → 1-(3-Methoxy-4-nitro-phenyl)-[4,4']bipiperidine

HRID 604289Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1.[OH-].[Na+].[Br-].C([NH3+])CCC>O.C1(C)C=CC=CC=1>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:13]2[CH2:18][CH2:17][CH:16]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-fluoro-2-methoxy-1-nitrobenzene (1.02 g, 5.97 mmol), [4,4′]bipiperidinyl (3.6 g, 14.9 mmol), 2N sodium hydroxide (30 mL), toluene (15 mL) and n-butylammonium bromide (96 mg, 0.30 mmol) is vigorously stirred at 80° C. for 18 hours. After 10 mL of water is added, the mixture is filtrated. The residue is washed with water and then dried to give 1-(3-methoxy-4-nitro-phenyl)-[4,4′]bipiperidine (1.79 g, 94% yield) as yellow solids.

Workup

filtrationthe mixture is filtrated
washThe residue is washed with water
customdried

Sources & evidence

ORD record: ord-b836616cf90d4ee690a8c306222371ac
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910585B2

Reaction notes

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