1-Chloroethyl chloroformate → HCID 10332074, compound

HRID 1743864Notes

Reaction equation

HRID 1743864 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:11][CH2:12][N:13](C)[CH2:14][CH2:15][N:6]3[C:7]=2[C:3]=1[C:4]1[CH2:19][CH2:18][CH2:17][C:5]=13.ClC(OC(Cl)C)=O>ClC(Cl)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][N:6]3[C:7]=2[C:3]=1[C:4]1[CH2:19][CH2:18][CH2:17][C:5]=13

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10422650HCID 10422650, compound

Product 1

HCID 10332074HCID 10332074, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 8-fluoro-3-methyl-2,3,4,5,10,11-hexahydro-1H,9H-cyclopenta[b][1,4]diazocino[7,8,1-hi]indole (0.90 g, 3.48 mmole) in dichloroethane (200 mL) was added 1-chloroethyl chloroformate (1.5 mL, 13.8 mmole) and the mixture refluxed for 24 hours. The reaction mixture was then cooled to room temperature and the solvent removed in vacuo and replaced with methanol (200 mL) and refluxed for another 3 h. The reaction mixture was 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% to 3% methanol in dichloromethane) provided 0.59 g of the title compound as a white solid. 0.18 g of the above solid was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 199-200° C. MS (ES) m/z 245.11 ([M+H]+), MS (ES) m/z 286.14 ([M+ACN+H]+).

Workup

  1. temperaturethe mixture refluxed for 24 hours
  2. customthe solvent removed in vacuo
  3. temperaturerefluxed for another 3 h
  4. temperatureThe reaction mixture was 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% to 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3fd4f34a6ff24e109a420994a9184ff1
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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