Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 618292Notes

Reaction equation

HRID 618292 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(Cl)Cl>[CH2:5]([O:4][C:2]([N:16]1[CH2:17][CH2:18][CH:13]([OH:12])[CH2:14][CH2:15]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 79341Piperidin-4-ol

Product 1

HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylateYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (35.3 ml, 0.25 moles) in 25 ml of methylene chloride was added dropwise under nitrogen over three hours to a solution of 4-hydroxypiperidine (25 g, 0.25 moles) and triethylamine (34.5 ml, 0.25 moles) in 500 ml of methylene chloride at ice bath temperature. After the addition the reaction was stirred at ice bath temperature for four hours and at room temperature overnight. The reaction was then extracted two times with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 53.1 g (90%) of the tide compound as a light yellow oil.

Workup

  1. additionAfter the addition the reaction
  2. customat room temperature
  3. customovernight
  4. extractionThe reaction was then extracted two times with 1N HCl
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-aa51a32112474e0ab7824b9c58472312
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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