Ethyl chloroformate → HCID 53942559, compound

HRID 2260148Notes

Reaction equation

HRID 2260148 reaction equation
C[N:2]1[CH2:20][CH2:19][N:5]2[C:6]3[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=3[CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C@H:4]2[CH2:3]1.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C=CC=CC=1>[CH2:3]1[C@@H:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][C:7]3[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=3[N:5]2[CH2:19][CH2:20][N:2]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 154315Dibenzo(c,f)pyrazino(1,2-a)azepine, 1,2,3,4,10,14b-hexahydro-2-methyl-, (14bS)-

Product 1

HCID 53942559HCID 53942559, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 5.52 g of (S)-1,2,3.4,10,14b-hexahydro-2-methyldibenzo[c,f]pyrazino[1,2-a]azepine (prepared as described in preparation 6) in 30 ml of toluene was added dropwise to a solution of 6.8 g of ethyl chloroformate in 50 ml of toluene at 80° C. over a period of 10 minutes, and the mixture was heated under reflux for 3 hours. At the end of this time, the crystals which precipitated were removed by filtration, and solvent was removed from the filtrate by evaporation under reduced pressure, to give 6.57 g (yield 98%) of the title compound as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAt the end of this time, the crystals which precipitated
  4. customwere removed by filtration, and solvent
  5. customwas removed from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7696a1471f5a449693f22e4edb31aeb6
Source dataset
uspto-grants-1995_12
Patent number
US05476848

Reaction notes

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