Nicotinoyl chloride → HCID 57271128, compound

HRID 648659Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[N:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH:22]([CH:26]([C:39]([NH2:41])=[O:40])[C:27]2[CH:38]=[CH:37][C:30]([C:31]([O:33][CH2:34][CH2:35][OH:36])=[O:32])=[CH:29][CH:28]=2)[CH2:23][CH2:24][CH3:25])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(Cl)Cl.C(N(CC)CC)C>[N:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH:22]([CH:26]([C:39]([NH2:41])=[O:40])[C:27]2[CH:38]=[CH:37][C:30]([C:31]([O:33][CH2:34][CH2:35][O:36][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=3)=[O:32])=[CH:29][CH:28]=2)[CH2:23][CH2:24][CH3:25])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 0.7 gm (4.68 m mol) of nicotinic acid chloride in 20 ml of methylene chloride was rapidly added dropwise to a stirred solution of 2.0 gm (4.56 m mol) of 2-hydroxyethyl 4-[(1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-benzoate in 40 ml of methylene chloride and 0.7 ml (4.81 m mol) of triethylamine. The resulting mixture was stirred at 20° C. for two and one-half hours and then extracted with water, and the organic phase was subsequently dried, filtered, and evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel [toluene/acetone (5:1)].

Workup

extractionextracted with water
customthe organic phase was subsequently dried
filtrationfiltered
customevaporated in vacuo
customThe evaporation residue was purified by column chromatography on silica gel [toluene/acetone (5:1)]

Sources & evidence

ORD record: ord-573012ddfeb640e2b1cacac3572bf49d
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04735959

Reaction notes

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