Pyridine → N-benzoyl-4-hydroxypiperidine

HRID 373145Notes

Reaction equation

HRID 373145 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.N1C=CC=CC=1>ClCCl>[C:1]([N:14]1[CH2:15][CH2:16][CH:11]([OH:10])[CH2:12][CH2:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 79341Piperidin-4-ol

Product 1

HCID 9877704N-benzoyl-4-hydroxypiperidineYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 73.1 g (520 mmol) of benzoyl chloride in 70 ml of dichloromethane was added dropwise to a solution of 50.0 g (495 mmol) of 4-hydroxypiperidine and 260 ml of pyridine in 260 ml of dichloromethane at 0° to 15° C. The mixture was stirred at room temperature for 3 h and white crystals (pyridine hydrochloride) thus precipitated were filtered out. The filtrate was concentrated and a remaining oil was purified by silica gel column chromatography (CHCl3 :CH3OH=95:5) to give 79.8 g (yield: 79%) of the intended compound:

Workup

  1. customwhite crystals (pyridine hydrochloride) thus precipitated
  2. filtrationwere filtered out
  3. concentrationThe filtrate was concentrated
  4. customa remaining oil was purified by silica gel column chromatography (CHCl3 :CH3OH=95:5)

Sources & evidence

ORD record
ord-6377cc0ea94248b3a2972e7350b45ee5
Source dataset
uspto-grants-1992_11
Patent number
US05162347

Reaction notes

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