Ethyl chloroformate → HCID 131722384, compound

HRID 635168Notes

Reaction equation

HRID 635168 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[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:4]2[CH2:3]1.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C=CC=CC=1>[CH3:26][CH2:25][O:24][C:22]([CH:3]1[CH:4]2[N:5]([C:6]3[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=3[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=32)[CH2:19][CH2:20][NH:2]1)=[O:23]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 1911112-Methyl-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrazino[1,2-d][1,4]oxazepine

Product 1

HCID 131722384HCID 131722384, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-methyl-(1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrazino[1,2-d][1,4]oxazepine) (2.0 g, 7.5 mmol, prepared similarly as described in Neth. Appl. 6709520, Chem. Abs. 70, 115192 (1969)) in toluene (12 ml) was added drop wise to a stirred solution of ethyl chloroformate (1.26 g, 1.1 ml, 11.7 mmol) in toluene (8 ml) at 60° C. The mixture was heated at reflux temperature for 2 h. After cooling, the mixture was washed with a saturated solution of sodium bicarbonate (2×10 ml), water (10 ml), dried (MgSO4) and evaporated. The residue (2.5 g) was purified by column chromatography on silica gel (50 g) using benzene as eluent to give 1.95 g (80%) of 2-ethoxycarbonyl-(1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrazino[1,2-d][1,4]oxazepine) as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureAfter cooling
  4. washthe mixture was washed with a saturated solution of sodium bicarbonate (2×10 ml), water (10 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue (2.5 g) was purified by column chromatography on silica gel (50 g)

Sources & evidence

ORD record
ord-c613e094a59d4e099ef2af218ae1a233
Source dataset
uspto-grants-2001_02
Patent number
US06187770B1

Reaction notes

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