Benzoyl chloride → 4-Piperidineethanol, 1-benzoyl-
Reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[OH-].[Na+]>ClCCl.C(N(CC)CC)C.O1CCOCC1.O>[C:1]([N:16]1[CH2:17][CH2:18][CH:13]([CH2:12][CH2:11][OH:10])[CH2:14][CH2:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
Benzoyl chloride (25.8 ml) in dichloromethane (20 ml) was added dropwise over 30 minutes to a mixture of 4-(2-hydroxyethyl)piperidine (26 g) in dichloromethane (250 ml) and triethylamine (16.3 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred at this temperature for 1 hour. The mixture was washed with sodium bicarbonate solution and then dried and evaporated to give a colourless oil. The oil was dissolved in 1,4-dioxane (250 ml) and then a solution of sodium hydroxide (5.0 g) in water (20 ml) was added and the mixture stirred at ambient temperature for 16 hours and then at 60° C. for 6 hours. The mixture was evaporated to near dryness, basified with 2M sodium hydroxide solution and the product extracted into dichloromethane to give 1-benzoyl-4-(2-hydroxyethyl)piperidine as an oil.
Workup
- washThe mixture was washed with sodium bicarbonate solution
- customdried
- customevaporated
- customto give a colourless oil
- stirringthe mixture stirred at ambient temperature for 16 hours
- waitat 60° C. for 6 hours
- customThe mixture was evaporated
- extractionthe product extracted into dichloromethane
Sources & evidence
- ORD record
- ord-570fbef5633544ffa44d58546e192736
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05760035
Reaction notes
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