Potassium Cyanide → cyclohexyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

HRID 1154447Notes

Reaction equation

HRID 1154447 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+]>C1(O)CCCCC1>[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][CH:19]3[CH2:4][CH2:3][CH2:2][CH2:7][CH2:20]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 54094222cyclohexyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent2×

Procedure

12 g (35 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 and 1 g of powdered potassium cyanide in 120 ml of cyclohexanol are stirred at 130° for 18 hours, in each case about 10 ml of cyclohexanol being distilled off three times in the course of the reaction. The mixture is subsequently evaporated, the residue is taken up in chloroform, washed with water, dried over magnesium sulphate and evaporated. By column chromatography on silica gel there is obtained cyclohexyl (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 166°-167°.

Workup

  1. distillationdistilled off three times
  2. customin the course of the reaction
  3. customThe mixture is subsequently evaporated
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-188e9f5a7782441483e3ffe2bb11d553
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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