1-Chloroethyl chloroformate → HCID 10376495, compound

HRID 1743831Notes

Reaction equation

HRID 1743831 reaction equation
C[N:2]1[CH2:15][CH2:14][C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]2[CH2:16][CH2:17][CH2:18][CH:6]2[N:5]3[CH2:4][CH2:3]1.ClC(OC(Cl)C)=O>ClC(Cl)C>[CH2:4]1[N:5]2[C:13]3[C:8]([CH:7]4[CH2:16][CH2:17][CH2:18][CH:6]42)=[CH:9][CH:10]=[CH:11][C:12]=3[CH2:14][CH2:15][NH:2][CH2:3]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10354397HCID 10354397, compound

Product 1

HCID 10376495HCID 10376495, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-methyl-2,3,4,5,9,10,11,11a-octahydro-1H,8bH-cyclopenta[b][1,4]diazocino[7,8,1-hi]indole (0.40 g, 1.6 mmole) in dichloroethane (80 mL) was added 1-chloroethyl chloroformate (1.2 mL, 10.8 mmole) and the solution refluxed for 24 hours under nitrogen. The reaction mixture was cooled to room temperature and the solvent removed in vacuo and replaced with methanol (200 mL) and refluxed for another 3 hours under nitrogen. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica gel, 1.5% methanol in dichloromethane) to provide 0.27 g of the title compound as an off-white solid. A THF solution of this compound was further treated with hydrogen chloride to provide 0.22 g of a hydrochloride salt, mp 137-140° C. MS (ESI) m/z 229 ([M+H]+).

Workup

  1. temperaturethe solution refluxed for 24 hours under nitrogen
  2. customthe solvent removed in vacuo
  3. temperaturerefluxed for another 3 hours under nitrogen
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by flash column chromatography (silica gel, 1.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e43c2b2eeaa34bff8b2e7daa1d430c4c
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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