Ethyl chloroformate → HCID 13450726, compound

HRID 1379990Notes

Reaction equation

HRID 1379990 reaction equation
C[N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:11][CH2:10][C:9]2=[O:25])[CH2:4][CH2:3]1.Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[CH2:30]([O:29][C:27]([N:2]1[CH2:3][CH2:4][CH:5]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:11][CH2:10][C:9]2=[O:25])[CH2:6][CH2:7]1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 566582H-1,4-Benzodiazepin-2-one, 1,3-dihydro-1-(1-methyl-4-piperidinyl)-5-phenyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 13450726HCID 13450726, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 98 mg (0.29 mmol) of 1,3-dihydro-1-(1-methyl-4-piperidinyl)-5-phenylbenzodiazepin-2-one 3, 0.084 ml (0.29×3 mmol) of ethyl chloroformate and 54.3 mg (0.29×2.2 mmol) of sodium hydrogencarbonate in 5 ml of benzene is refluxed under heating for 7 hours. The reaction mixture is poured into ice water and extracted with methylene chloride. The organic layer is washed with water dried over anhydrous magnesium sulfate and concentrated to give 114 mg of 1-(1-ethoxycarbonyl-4-piperidinyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 12 as powders. The yield is 100%.

Workup

  1. temperatureunder heating for 7 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-658a4ded9abb4cba9f373e94aa2792b3
Source dataset
uspto-grants-1986_04
Patent number
US04579685

Reaction notes

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