1-Chloroethyl chloroformate → HCID 68708639, compound

HRID 645484Notes

Reaction equation

HRID 645484 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][C:9]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:14][CH2:13][N:12](CC2C=CC(OC)=CC=2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:32]([O:34][CH:35]([Cl:37])[CH3:36])=[O:33]>C(Cl)Cl>[Cl:37][CH:35]([O:34][C:32]([N:12]1[CH2:13][CH2:14][C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:30])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][CH2:11]1)=[O:33])[CH3:36]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 68708945HCID 68708945, compound

Product 1

HCID 68708639HCID 68708639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(4-methoxy-benzyl)-4-phenylpiperidin-4-ylmethyl]carbamic acid tert-butyl ester (3.2 mmol) in CH2Cl2 is added 1-chloroethyl chloroformate (4.7 mmol), then the mixture is stirred at room temperature for 2.5 h. After the bulk of solvent is concentrated in vacuo, the residue suspended in ether and filtered. After the filtrate is concentrated in vacuo, the residue is suspended in hexane and filtered. The filtrate is concentrated in vacuo to give the 4-(tert-butoxycarbonylaminomethyl)-4-phenylpiperidine-1-carboxylic acid 1-chloroethyl ester, which is directly used for the next reaction without further purification.

Workup

  1. concentrationAfter the bulk of solvent is concentrated in vacuo
  2. filtrationfiltered
  3. concentrationAfter the filtrate is concentrated in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-72f8b51875a340da94a028b88605c3f6
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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