1-Chloroethyl chloroformate → HCID 22224977, compound

HRID 1744816Notes

Reaction equation

HRID 1744816 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-3cf0aa12454d49ada11716cb01095b5a
Source dataset
uspto-grants-2006_03
Patent number
US07019001B2

Reaction notes

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