4-(1-Pyrrolidinyl)piperidine → 1-(3-Methoxy-4-nitro-phenyl)-4-pyrrolidin-1-yl-piperidine

HRID 2222125Notes

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.[N:13]1([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:21]2[CH2:22][CH2:23][CH:18]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:19][CH2:20]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

200 mg (1.170 mmol) 4-fluoro-2-methoxy-1-nitro-benzene are dissolvedjin 1 ml NMP, combined with 198 mg (1.284 mmol) 4-pyrrolidin-1-yl-piperidine and 300 μl diisopropylethylamine and stirred for 17 h at 80° C. Then the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier material used is C18-RP gel and a gradient is run through which consists of 95% water and 5% acetonitrile at the starting point and 5% water and 95% acetonitrile at the finishing point.

Workup

customThe crude product is purified by column chromatography

Sources & evidence

ORD record: ord-4ccbb891dc9e405284dddacad9d05799
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371753B2

Reaction notes

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