1-Chloroethyl chloroformate → HCID 9970596, compound

HRID 1743849Notes

Reaction equation

HRID 1743849 reaction equation
[Cl:1][C:2]1[C:14]2[CH2:15][CH2:16][N:17](C)[CH2:18][CH2:19][N:12]3[C:13]=2[C:5]([C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=23)=[CH:4][CH:3]=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[Cl:1][C:2]1[C:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:12]3[C:13]=2[C:5]([C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10108205HCID 10108205, compound

Product 1

HCID 9970596HCID 9970596, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 6-chloro-3-methyl-2,3,4,5,9,10,11,12-octahydro-1H-[1,4]diazocino[7,8,1-jk]carbazole (0.36 g, 1.25 mmole) in dichloroethane (80 mL) was added 1-chloroethyl chloroformate (1.2 mL, 10.8 mmole) and the mixture refluxed for 24 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo and replaced with methanol (25 mL) and refluxed for another 3 hours. The reaction mixture was then cooled to room temperature and the solvent removed in vacuo. The dark residue was dissolved in methylene chloride (200 mL) and washed with aqueous sodium hydroxide (1N, 150 mL), saturated sodium chloride (150 mL), dried (sodium sulfate) and concentrated. Purification by flash column chromatography (silica gel, 1.5% methanol in dichloromethane) provided 0.30 g of the title compound. 80 mg of this was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 208-210° C. MS (ESI) m/z 275 ([M+H]+).

Workup

  1. temperaturethe mixture refluxed for 24 hours
  2. customthe solvent removed in vacuo
  3. temperaturerefluxed for another 3 hours
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. customthe solvent removed in vacuo
  6. dissolutionThe dark residue was dissolved in methylene chloride (200 mL)
  7. washwashed with aqueous sodium hydroxide (1N, 150 mL), saturated sodium chloride (150 mL)
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated
  10. customPurification by flash column chromatography (silica gel, 1.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b4ad3e1148a545e8bb4b4aaefef5ca50
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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