1-Chloroethyl chloroformate → HCID 22224977, compound

HRID 2086555Notes

Reaction equation

HRID 2086555 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:14][OH:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[CH2:16]([C:11]1([CH2:14][OH:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22225015HCID 22225015, compound

Product 1

HCID 22224977HCID 22224977, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1,4-Dibenzyl-4-hydroxymethyl-piperidine (1.0 g, 3.4 mmol) in dichloromethane (20 ml) are treated with 1-chloroethyl-chloroformate (0.48 ml, 4.3 mmol, dissolved in 1.5 ml dichloromethane) and the resulting solution is stirred at 0° C. for 30 min. The solvent is removed in vacuo and the resulting residue refluxed in methanol (20 ml) for 40 min. After removel of the volatile components in vacuo, the title compound is isolated by flash chromatography (silca, eluent dichloromethane/methanol/triethylamine (9:1:0.1, then 4:1:0.1 followed by 3:1:0.1)) as a brown resin in 40% yield. MS 206(M+H+).

Workup

  1. customThe solvent is removed in vacuo
  2. temperaturethe resulting residue refluxed in methanol (20 ml) for 40 min

Sources & evidence

ORD record
ord-bd35951b91d34967a9806ec1e4d3f129
Source dataset
uspto-grants-2004_04
Patent number
US06727247B2

Reaction notes

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