Triethylamine → Benzyl 4-Hydroxy-1-piperidinecarboxylate

HRID 747755Notes

Reaction equation

HRID 747755 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C(N(CC)CC)C>ClCCl>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4][CH2:3]1

Participants

5

Reactant 3

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

Product 1

HCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

25.0 g (247 mmol) of 4-hydroxypiperidine was dissolved in 800 ml of dichloromethane. 38 ml (266 mmol) of benzyl chloroformate and 75 ml (538 mmol) of triethylamine were added to the solution at 0° C., and they were stirred at room temperature for 15 hours. After the treatment with dichloromethane as the extractant in an ordinary manner, an oily residue was obtained. This residue was subjected to the subsequent reaction without further purification.

Workup

  1. customThis residue was subjected to the subsequent reaction without further purification

Sources & evidence

ORD record
ord-9d79f3df8f804bc79cc7e1d9631c9c18
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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