Benzyl Bromide → N-benzyl-3-(m-trifluoromethylphenyl)-piperidine

HRID 128220Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[Ag]=O.CC(C)=O>[CH2:17]([N:11]1[CH2:12][CH2:13][CH2:14][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=2)[CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.2 g of silver oxide were added to a mixture of 4.6 g of 3-(m-trifluoromethylphenyl)-piperidine and 22 ml of acetone and the mixture was cooled on an ice water bath while 2.55 ml (≃3.6 g) of benzyl bromide was added dropwise over 10 minutes at a temperature less than 10° C. The mixture was stirred at 0° C. for one hour and was filtered. The filtrate was evaporated to dryness under reduced presssure to obtain 7 g of raw product which was chromatographed over silica gel. Elution with an 85-10-5 cyclohexane-chloroformtriethylamine mixture and evaporation to dryness under reduced pressure yielded 4.99 g of N-benzyl-3-(m-trifluoromethylphenyl)-piperidine.

Workup

additionwas added dropwise over 10 minutes at a temperature less than 10° C
filtrationwas filtered
customThe filtrate was evaporated to dryness under reduced presssure
customto obtain 7 g of raw product which
customwas chromatographed over silica gel
washElution
customwith an 85-10-5 cyclohexane-chloroformtriethylamine mixture and evaporation to dryness under reduced pressure

Sources & evidence

ORD record: ord-09e223c5d4e34f3d887320c2763130f9
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04259337

Reaction notes

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