Benzyl chloroformate → HCID 20214847, compound

HRID 1905635Notes

Reaction equation

HRID 1905635 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][C:39]([Cl:42])=[CH:38][CH:37]=3)[C:17]=2[CH:43]=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(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:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=3)[C:17]=2[CH:43]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 20214827HCID 20214827, compound

Product 1

HCID 20214847HCID 20214847, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

20 ml (0.06 mole) of a 50 percent strength solution of benzyl chloroformate in toluene are added to a mixture of 9.5 g (0.02 nole) of 7-chloro-5-(4-chlorophenyl)-1'-benzyl-spiro[1H-1,4-benzodiazepine-3,4'-piperidin]-2(3H)-one and 5 g (0.06 mole) of NaHCO3 in 150 ml of methylene chloride. 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 percent strength NaHCO3 solution. After drying over Na2SO4, the organic phase is filtered and the solvent is evaporated off. The oily residue is made to crystallise with petroleum ether. The compound is filtered off with suction, boiled up with n-hexane 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 percent strength NaHCO3 solution
  6. dry with materialAfter drying over Na2SO4
  7. filtrationthe organic phase is filtered
  8. customthe solvent is evaporated off
  9. customto crystallise with petroleum ether
  10. filtrationThe compound is filtered off with suction
  11. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-8fd9800ebf9c4e2abeca077ed6970b62
Source dataset
uspto-grants-1987_03
Patent number
US04647560

Reaction notes

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