Ethyl chloroformate → HCID 21442798, compound

HRID 328584Notes

Reaction equation

HRID 328584 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:9]1)C1C=CC=CC=1.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].[OH-].[Na+]>C1C=CC=CC=1>[CH2:34]([O:33][C:31]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2[C:16]3[CH:29]=[CH:28][CH:27]=[CH:26][C:17]=3[CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]2=3)[CH2:9]1)=[O:32])[CH3:35]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 13277198HCID 13277198, compound

Product 1

HCID 21442798HCID 21442798, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-(4-benzyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine (1.62 g) and ethyl chloroformate (1.44 g) in benzene was stirred under reflux for 8 hours. The reaction mixture was cooled, admixed with 10% aqueous sodium hydroxide and extracted with benzene. The benzene extract was dried over anhydrous sodium sulfate and evaporated to afford 5-(4-ethoxycarbonyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oily substance. To a solution of the oil in ethanol was added 30% aqueous sodium hydroxide, and the resulting mixture was stirred at 65° C for 5 hours. The reaction mixture was cooled and extracted with benzene. The benzene extract was dried over anhydrous sodium sulfate and evaporated to afford 5-(2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oily substance. M.P. 194.5°-195.5° C (oxalate).

Workup

  1. temperatureunder reflux for 8 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with benzene
  4. extractionThe benzene extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-0d5030c009204049928eb0c5cc06bb75
Source dataset
uspto-grants-1977_04
Patent number
US04017621

Reaction notes

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