Phenyl chloroformate → HCID 20087949, compound

HRID 275387Notes

Reaction equation

HRID 275387 reaction equation
[CH2:1]([C:3]1([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22](C)[CH2:21][CH2:20]2)[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[CH2:6][CH2:5][O:4]1)[CH3:2].C1(OC([Cl:35])=O)C=CC=CC=1>C1(C)C=CC=CC=1>[ClH:35].[ClH:35].[CH2:1]([C:3]1([CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[CH2:6][CH2:5][O:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 20087959HCID 20087959, compound

Product 1

HCID 20087949HCID 20087949, compoundYield 209.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 20 g of crude 1-[2-(1-ethyl-3,4-dihydro -6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]-4-methylpiperazine and 7.5 g of phenylchloroformate in 150 ml of toluene was refluxed for 4 h. The toluene was evaporated, and the residue dissolved in a mixture of 150 ml of ethanol and 150 ml of 50% aqueous sodium hydroxide and refluxed for 2 h. The ethanol was evaporated and the residue dissolved in diethyl ether. The solution was washed, dried and concentrated and the residue was dissolved in acetone with anhydrous hydrochloric acid to yield 20.4 g (87.9%) of crude 1-[2-(1-ethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran-1-yl)ethyl]piperazine dihydrochloride.

Workup

  1. temperaturewas refluxed for 4 h
  2. customThe toluene was evaporated
  3. dissolutionthe residue dissolved in a mixture of 150 ml of ethanol and 150 ml of 50% aqueous sodium hydroxide
  4. temperaturerefluxed for 2 h
  5. customThe ethanol was evaporated
  6. dissolutionthe residue dissolved in diethyl ether
  7. washThe solution was washed
  8. customdried
  9. concentrationconcentrated
  10. dissolutionthe residue was dissolved in acetone with anhydrous hydrochloric acid

Sources & evidence

ORD record
ord-4dbb826afe1343979cafad608440a651
Source dataset
uspto-grants-1995_02
Patent number
US05393759

Reaction notes

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