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Triethylamine → Ethyl n-(1-benzyl-4-hydroxy-4-piperidyl)methylcarbamate

HRID 430609
Notes
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Reaction equation

HRID 430609 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([CH2:21][NH2:22])([OH:20])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>ClCCl>[CH2:7]([N:14]1[CH2:15][CH2:16][C:17]([CH2:21][NH:22][C:2](=[O:3])[O:4][CH2:5][CH3:6])([OH:20])[CH2:18][CH2:19]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 104210264-(Aminomethyl)-1-benzylpiperidin-4-ol

Product 1

HCID 18351343Ethyl n-(1-benzyl-4-hydroxy-4-piperidyl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14.75 g of ethyl chloroformate in 125 ml of dichloromethane is added, at 0° C., to a solution of 30 g of 1-benzyl-4-aminomethyl-piperidin-4-ol and 13.8 g of triethylamine in 250 ml of dichloromethane. After 10 minutes' contact, the reaction mixture is washed with 0.1N sodium hydroxide solution and then dried over MgSO4. Concentration under reduced pressure enables the expected product to be isolated.

Workup

  1. washthe reaction mixture is washed with 0.1N sodium hydroxide solution
  2. dry with materialdried over MgSO4
  3. concentrationConcentration under reduced pressure
  4. customto be isolated

Sources & evidence

ORD record
ord-5a9f4d55fb364f7e8fb701b31aeeadcf
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06323217B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes