Benzene, 1-chloro-4-fluoro- → 1-Benzyl-4-(p-chlorophenoxy)piperidine
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=1>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
A solution of 21.6 g of 1-benzyl-4-piperidinol in 75ml. of dimethylformamide is added slowly to a stirred suspension of 8.7 g of a 50% oil dispersion of sodium hydride in 225 ml. of dimethylformamide at 60°-70° C. After addition is complete stirring and heating are continued until no more hydrogen gas is liberated. A solution of 19.6 g of 1-chloro-4-fluorobenzene in 75 ml. of dimethylformamide is added, and the solution is permitted to stir at 65°-70° C. for 16 hours. After cooling to ambient temperature, the solution is poured into 600 ml. of water, the aqueous solution is extracted with benzene, the benzene extracts are dried, and the benzene is removed under reduced pressure, leaving a yellow oil of 1-benzyl-4-(p-chlorophenoxy)piperidine.
Workup
- customat 60°-70° C
- additionAfter addition
- temperatureheating
- stirringto stir at 65°-70° C. for 16 hours
- additionthe solution is poured into 600 ml
- extractionof water, the aqueous solution is extracted with benzene
- dry with materialthe benzene extracts are dried
- customthe benzene is removed under reduced pressure
Sources & evidence
- ORD record
- ord-fcf69e8b36014cb8b24ac1ad22295f2d
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04031221
Reaction notes
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