Benzyl chloroformate → HCID 13631909, compound

HRID 1905627Notes

Reaction equation

HRID 1905627 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[NH:34][C:33](=[O:35])[C:20]3([CH2:25][CH2:24][N:23](CC4C=CC=CC=4)[CH2:22][CH2:21]3)[N:19]=[C:18]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:17]=2[CH:42]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[NH:34][C:33](=[O:35])[C:20]3([CH2:25][CH2:24][N:23]([C:2]([O:4][CH2:5][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)=[O:3])[CH2:22][CH2:21]3)[N:19]=[C:18]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:17]=2[CH:42]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 13631908HCID 13631908, compound

Product 1

HCID 13631909HCID 13631909, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

10 g (0.029 mole) of a 50% strength solution of benzyl chloroformate in toluene are added to a mixture of 4.0 g (0.0093 mole) of 7-chloro-5-phenyl-1'-benzyl-spiro[1H-1,4-benzodiazepine-3,4'-piperidin]-2-(3H)-one and 2.4 g (0.029 mole) of finely powdered NaHCO3 in 80 ml of absolute chloroform. The reaction mixture is boiled for 3 hours, with reflux cooling. It is then poured onto ice and the organic phase is separated off and washed twice with 10% strength NaHCO3 solution. After drying over Na2SO4, the mixture is filtered and the solvent is evaporated off. A pale brown-colored remains, and is crystallized with petroleum ether. The compound is filtered off with suction, washed with petroleum ether and dried at 60° C. in vacuo.

Workup

  1. temperaturewith reflux
  2. temperaturecooling
  3. additionIt is then poured onto ice
  4. customthe organic phase is separated off
  5. washwashed twice with 10% strength NaHCO3 solution
  6. dry with materialAfter drying over Na2SO4
  7. filtrationthe mixture is filtered
  8. customthe solvent is evaporated off
  9. customA pale brown-colored remains, and is crystallized with petroleum ether
  10. filtrationThe compound is filtered off with suction
  11. washwashed with petroleum ether
  12. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-e7c7aef0b49e4b32a69baafb383d9558
Source dataset
uspto-grants-1987_03
Patent number
US04647560

Reaction notes

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