Hydrogen Bromide → HCID 20214849, compound

HRID 1905634Notes

Reaction equation

HRID 1905634 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:29]3[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=3[NH:27][C:26](=[O:35])[C:10]3([CH2:15][CH2:14][N:13](C(OCC4C=CC=CC=4)=O)[CH2:12][CH2:11]3)[N:9]=2)=[CH:4][CH:3]=1.Br>>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]2[NH:27][C:26](=[O:35])[C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:29]=2[CH:30]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 20214847HCID 20214847, compound

Product 1

HCID 20214849HCID 20214849, compound

Procedure

8.8 g (0.017 mole) of 5-(4-chlorophenyl)-7-chloro-1'-benzyloxycarbonyl-spiro[1H-1,4-benzodiazepine-3,4'-piperidin]-2(3H)-one are suspended in 150 ml of petroleum either (boiling range: 60°-80° C.), and 10 ml of 38 percent strength HBr/glacial acetic acid solution are added at 20° C., with stirring. The reaction mixture is stirred at room temperature for 6 hours and the crystalline product is filtered off with suction and rinsed with petroleum ether. The product is dissolved in water and the aqueous solution is shaken with diethyl ether and rendered alkaline with concentrated aqueous ammonia solution. The base which separates out is taken up in methylene chloride and the organic phase is dried over Na2SO4 and filtered. After evaporating off the solvent, the base is obtained in form of pale yellow crystals.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 6 hours
  2. filtrationthe crystalline product is filtered off with suction
  3. washrinsed with petroleum ether
  4. dissolutionThe product is dissolved in water
  5. stirringthe aqueous solution is shaken with diethyl ether
  6. dry with materialthe organic phase is dried over Na2SO4
  7. filtrationfiltered
  8. customAfter evaporating off the solvent
  9. customthe base is obtained in form of pale yellow crystals

Sources & evidence

ORD record
ord-1ffb6ab721aa4b0386140dc77db7e2d5
Source dataset
uspto-grants-1987_03
Patent number
US04647560

Reaction notes

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