Benzoyl chloride → N-benzoyl-4-hydroxypiperidine

HRID 544252Notes

Reaction equation

HRID 544252 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.C(=O)([O-])[O-].[Na+].[Na+]>O>[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 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 9877704N-benzoyl-4-hydroxypiperidineYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

In this reference example, 7.03 g of benzoyl chloride was added dropwise to a mixture of 5.05 g of 4-hydroxypiperidine, 6.36 g of sodium carbonate and 60 ml of water at 10° C. with stirring. After the addition, the mixture was maintained at 5° C. for 2 hours. The reaction mixture was filtered, and then filtrate was extracted with dichloromethane. The extract was concentrated, and ether was added to crystallize, whereby 9.20 g of 1-benzoyl-4-hydroxypiperidine was obtained (yield: 90.1%).

Workup

  1. additionAfter the addition
  2. filtrationThe reaction mixture was filtered
  3. extractionfiltrate was extracted with dichloromethane
  4. concentrationThe extract was concentrated
  5. additionether was added
  6. customto crystallize

Sources & evidence

ORD record
ord-a9b7dc2369884f3d9893afe343f82f4c
Source dataset
uspto-grants-1984_05
Patent number
US04448964

Reaction notes

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