Allyl chloroformate → 17518-99-9
Reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3].Br.Br[CH2:10][C:11](=[O:21])[CH2:12][C@H:13]1[C@H:18]([O:19][CH3:20])[CH2:17][CH2:16][CH2:15][NH:14]1.[Cl:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[Br:33])[N:29]=[CH:28][NH:27][C:26]2=[O:34]>>[Br:33][C:32]1[CH:31]=[C:30]2[C:25]([C:26](=[O:34])[N:27]([CH2:10][C:11]([CH2:12][CH:13]3[CH:18]([O:19][CH3:20])[CH2:17][CH2:16][CH2:15][N:14]3[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3])=[O:21])[CH:28]=[N:29]2)=[CH:24][C:23]=1[Cl:22]Participants
Procedure
The said known procedure comprises reacting trans 1-(3-methoxy-2-piperidyl)-2-propanone hydrobromide with hydrobromic acid as in U.S. Pat. No. 2,775,597 to form the trans 3-bromo-1-(3-methoxy-2-piperidyl)-2-propanone hydrobromide, reacting the latter with allyl chloroformate as indicated in J. Org. Chem., Vol. 20 (1955), p. 118-142 to block the nitrogen atom of the piperidine with allyloxycarbonyl by forming 1-allyloxycarbonyl-2-(ω-bromoacetonyl)-3-methoxypiperidine, condensing the latter with 6-chloro-7-bromo-3,4-dihydro-4-quinazolinone as described in French Pat. No. 1,550,956 to obtain 7-bromo-6-chloro-3-[3-(1-allyloxycarbonyl-3-methoxy-2-piperidyl)-acetonyl]-4(3H)-quinazolinone, subjecting the latter to hydrobromic acid as taught in French Pat. No. 1,550,956 to obtain 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-acetonyl]-4(3H)-quinazolinone hydrobromide and treating the latter with a base to form the corresponding free base which if desired may be salified with a non-toxic, pharmaceutically acceptable acid to form the desired acid addition salt.
Workup
- customby forming
Sources & evidence
- ORD record
- ord-55ede120ef45492d8cb1a248d0f142a4
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04252947
Reaction notes
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