1-Chloroethyl chloroformate → HCID 10353664, compound

HRID 1743829Notes

Reaction equation

HRID 1743829 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)[C:7]2[CH2:16][CH2:17][CH2:18][C: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]([C:7]4[CH2:16][CH2:17][CH2:18][C: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 10263687HCID 10263687, compound

Product 1

HCID 10353664HCID 10353664, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-methyl-2,3,4,5,10,11-hexahydro-1H,9H-cyclopenta[b][1,4]diazocino[7,8,1-hi]indole (90 mg, 0.36 mmole) in dichloroethane (10 mL) was added 1-chloroethyl chloroformate (0.15 mL, 1.3 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 (25 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 27 mg of the title compound as a light yellow oil. The oil was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 180-183° C., which contained a slight excess of fumaric acid. MS (ESI) m/z 227 ([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-17b3daa977b145c9b6bde7b5941162a1
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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