Potassium Cyanide → HCID 53661694, compound

HRID 1154459Notes

Reaction equation

HRID 1154459 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+]>OCC1CCCCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH:20]3[CH2:6][CH2:7][CH2:2][CH2:3][CH2:4]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 53890667ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxylate

Product 1

HCID 53661694HCID 53661694, compound

Reagents, catalysts & solvents 1

HCID 7507CyclohexanemethanolSolvent

Procedure

A mixture of 6.9 g (20 mmol) of ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxylate, 0.6 g (9.2 mmol) of potassium cyanide and 70 ml of hydroxymethyl-cyclohexane is stirred at 130° for 16 hours, a small amount of solvent being distilled off twice in the course of the reaction. The mixture is subsequently evaporated in a high vacuum, the residue is partitioned between water and chloroform, the chloroform solution is washed twice with saturated sodium chloride solution and dried over magnesium sulphate. After evaporation of the chloroform soluticn, the residue is crystallized from ethyl acetate/n-hexane, there being obtained cyclohexylmethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 123°-124° C.

Workup

  1. distillationa small amount of solvent being distilled off twice in the course of the reaction
  2. customThe mixture is subsequently evaporated in a high vacuum
  3. customthe residue is partitioned between water and chloroform
  4. washthe chloroform solution is washed twice with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customAfter evaporation of the chloroform soluticn
  7. customthe residue is crystallized from ethyl acetate/n-hexane, there

Sources & evidence

ORD record
ord-33caebf17e15493788fd2099418529ae
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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