1-Chloroethyl chloroformate → HCID 10354280, compound

HRID 1743832Notes

Reaction equation

HRID 1743832 reaction equation
C[N:2]1[CH2:19][CH2:18][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[N:5]([C:6]=23)[CH2:4][CH2:3]1.ClC(OC(Cl)C)=O>ClC(Cl)C>[CH2:4]1[N:5]2[C:6]3[C:11]([C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=42)=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:18][CH2:19][NH:2][CH2:3]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10354976HCID 10354976, compound

Product 1

HCID 10354280HCID 10354280, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-methyl-2,3,4,5,9,10,11,12-octahydro-1H-[1,4]diazocino[7,8,1-jk]carbazole (0.20 g, 0.79 mmole) in dichloroethane (15 mL) was added 1-chloroethyl chloroformate (0.80 mL, 7.2 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 (100 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 0.10 g of the title compound as a light yellow oil. The oil was further treated with one equivalent of fumaric acid in ethanol, the resulting solid collected by filtration and washed with ether to give 0.12 g of a fumarate salt, mp 174-176° C. MS (ESI) m/z 241 ([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-13fb2b617d334aaa849d56a8529a432b
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

Loading…