tert-Butyl 4-(methylamino)piperidine-1-carboxylate → tert-butyl 4-({-[(E)-2-(4'-chlorobiphenyl-4-ylcarbamoyl)vinyl]benzyl}methylamino)piperidine-1-carboxylate

HRID 735178Notes

Reaction equation

C[NH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:41])/[CH:31]=[CH:32]/[C:33]3[CH:38]=CC(CCl)=[CH:35][CH:34]=3)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1>CN(C=O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30](/[CH:31]=[CH:32]/[CH:33]([CH2:38][NH:2][CH:3]3[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]3)[C:34]3[CH:5]=[CH:4][CH:3]=[CH:8][CH:35]=3)=[O:41])=[CH:27][CH:28]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.5 g (2.34 mmol) of tert-butyl 4-methylaminopiperidine-1-carboxylate is added to a suspension of 300 mg (0.79 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide in 5 mL of DMF and the mixture is stirred for 18 hours at 80° C. Then the reaction mixture is poured onto water and the precipitate formed is suction filtered. Further purification is carried out by stirring out from a little methanol. Yield: 200 mg (45% of theory); C33H38ClN3O3 (M=560.13); melting point: 168° C.-169° C.; calc.: molecular ion peak (M+H)+: 560/562 (Cl); found: molecular ion peak (M+H)+: 560/562 (Cl).

Workup

additionThen the reaction mixture is poured onto water
customthe precipitate formed
filtrationfiltered
customFurther purification
stirringby stirring out from a little methanol

Sources & evidence

ORD record: ord-967537c06e3c41b19274ab1e13016194
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592373B2

Reaction notes

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