Hydrogen Bromide → 7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide

HRID 1414066Notes

Reaction equation

HRID 1414066 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:30])[N:7]([CH2:12][C:13]([CH2:15][CH:16]3[CH:21]([O:22]C)[CH2:20][CH2:19][CH2:18][N:17]3C(OCC=C)=O)=[O:14])[CH:8]=[N:9]2)=[CH:4][C:3]=1[Cl:31].Br>>[BrH:1].[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:30])[N:7]([CH2:12][C:13]([CH2:15][CH:16]3[CH:21]([OH:22])[CH2:20][CH2:19][CH2:18][NH:17]3)=[O:14])[CH:8]=[N:9]2)=[CH:4][C:3]=1[Cl:31]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 2028980617518-99-9

Product 1

HCID 628937-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-2-oxopropyl]quinazolin-4(3H)-one monohydrobromide

Procedure

Using the procedure of French Pat. No. 1,550,956, a solution of the product of Step D in an aqueous 48% hydrobromic acid solution was refluxed for an hour and was then evaporated to dryness. The residue in ethanol was refluxed for 30 minutes and the mixture was filtered to obtain dextrorotary 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-acetonyl]-4(3H)-quinazolinone hydrobromide with a specific rotation of [α]D20 =+6°±1° (c=1% in a 1--1 methanol-water mixture).

Workup

  1. customwas then evaporated to dryness
  2. temperatureThe residue in ethanol was refluxed for 30 minutes
  3. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-7aef124cc94140a68c9820a9d1d841a1
Source dataset
uspto-grants-1981_02
Patent number
US04252947

Reaction notes

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