Nicotinic Acid → HCID 12799178, compound

HRID 851155Notes

Reaction equation

ClC(OCC(C)C)=O.[C:9]([OH:17])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.Cl.Cl.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:44]=[CH:43][C:34]3[C:35]4[CH2:42][CH2:41][CH2:40][C:36]=4[C:37](=[O:39])[O:38][C:33]=3[CH:32]=2)[CH2:23][CH2:22]1.[OH-].[Na+]>O.C(N(CC)CC)C.ClCCl>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][O:30][C:31]3[CH:44]=[CH:43][C:34]4[C:35]5[CH2:42][CH2:41][CH2:40][C:36]=5[C:37](=[O:39])[O:38][C:33]=4[CH:32]=3)[CH2:23][CH2:22]2)=[O:17])[CH:11]=1

Participants

Conditions

Temperature: -10 °C

Procedure

1.3 ml. (0.01 mole) Isobutyl chloroformate, dissolved in 10 ml. dichloromethane, is added dropwise at -5° C. to -10° C. to a mixture of 1.23 g. (0.01 mole) nicotinic acid, 40 ml. dichloromethane and 1.4 ml. triethylamine. After stirring the reaction mixture for 15 minutes at -10° C., a slurry of 4.15 g. (0.01 mole) 7-[3-(4-aminopiperidino)-propoxy]-2,3-dihydrocyclopenta[c][1]benzopyran-4(1H)-one dihydrochloride in 30 ml. dichloromethane and 2.8 g. triethylamine is added thereto and the reaction mixture is further stirred for 30 minutes at -10° C., washed with water, mixed with an excess of ethereal hydrogen chloride solution, filtered and the precipitate obtained taken up in water and rendered alkaline with an aqueous solution of sodium hydroxide. There are thus obtained 2.8 g. (62% of theory) of the desired compound; m.p. 199°-200° C.

Workup

stirringthe reaction mixture is further stirred for 30 minutes at -10° C.
washwashed with water
additionmixed with an excess of ethereal hydrogen chloride solution
filtrationfiltered
customthe precipitate obtained

Sources & evidence

ORD record: ord-b5c10aa76305459daa55387baf943c7d
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04382943

Reaction notes

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