Triethylamine → 1-[5'-(4-fluoro-benzoyl)-3,4,5,6,3',6'-hexahydro-2H,2'H-[1,4']bipyridinyl-1'-yl]-ethanone

HRID 1917275Notes

Reaction equation

[N:1]1([C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:15])[CH3:14])[CH2:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(Cl)Cl>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([C:12]2[CH2:11][N:10]([C:13](=[O:15])[CH3:14])[CH2:9][CH2:8][C:7]=2[N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:29])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of crude 1-(3,4,5,6,3′,6′-hexahydro-2H,2′H-[1,4′]bipyridinyl-1′-yl)-ethanone in CH2Cl2 (1.5 L) was treated with Et3N (108 mL, 0.78 mol) and then cooled to 0° C. A solution of 4-fluorobenzoyl chloride (107 g, 0.68 mol) in CH2Cl2 (150 mL) was added over 1 h. The reaction mixture was stirred at rt for 2 h, then was concentrated to give a crude material which was directly used on next reaction. HPLC: RT=7.52 min. MS (ESI): exact mass calcd. for C19H23FN2O2, 330.17; m/z found, 331.0 [M+H]+.

Workup

concentrationwas concentrated

Sources & evidence

ORD record: ord-089028d887f241d59ccf62086811ebe6
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618288B2

Reaction notes

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