1-Chloroethyl chloroformate → HCID 63586081, compound

HRID 238291Notes

Reaction equation

HRID 238291 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:23])([OH:16])[CH2:12]2)C1C=CC=CC=1.ClC(OC(Cl)=O)C>CO>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:11]1([OH:16])[CH2:10][CH:9]2[NH:8][CH:13]([CH2:14][CH2:15]2)[CH2:12]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 67059926HCID 67059926, compound

Product 1

HCID 63586081HCID 63586081, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-Benzyl-3-(2-chloro-phenyl)-8-aza-bicyclo[3.2.1]octan-3-ol (0.30 g, 0.93 mmol) was dissolved in methanol (5 mL) and 1-chloroethylchloroformate (0.14 mL) was added. The mixture was heated at reflux for 6 hours and allowed to cool. The solvent was removed by evaporation under vacuum and the residue precipitated from ethyl acetate with ether to give a white solid (0.12 g, 56%). LCMS m/z 287.2 [M+H]+. R.T.=1.96 min (Analytical Method 4).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours
  3. temperatureto cool
  4. customThe solvent was removed by evaporation under vacuum
  5. customthe residue precipitated from ethyl acetate with ether

Sources & evidence

ORD record
ord-6e945488d83b46ca8611e188bf22f7ef
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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