Sodium Chloride → HCID 19390880, compound

HRID 1756674Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:5]([N:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[CH2:22]([N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-:36].[Na+]>O1CCCC1>[ClH:36].[ClH:36].[CH2:22]([N:29]1[CH2:30][CH:31]=[C:32]([C:2]2[CH:10]=[CH:9][C:5]([N:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=2)[CH2:33][CH2:34]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 10 g of p-bromo-N,N-dimethylaniline in 100 ml of tetrahydrofuran was chilled to -78° C., followed by addition of a hexane solution containing an equimolar amount of n-butyllithium. The mixture was stirred at -78° C. for 10 minutes, after which 9.5 g of N-benzyl-4-piperidone was added. The mixture was further stirred for 1 hour. The reaction mixture was then diluted with 100 ml of saturated aqueous sodium chloride solution and the organic layer was taken. From this layer, the solvent was distilled off, and 200 ml of concentrated hydrochloric acid was added to the oily residue. The mixture was heated at 100° C. with stirring for 6 hours. Finally, the solvent was distilled off and the residue was recrystallized from methanol to give 14 g of colorless crystals melting at 229°-232° C.

Workup

stirringThe mixture was further stirred for 1 hour
distillationFrom this layer, the solvent was distilled off
addition200 ml of concentrated hydrochloric acid was added to the oily residue
temperatureThe mixture was heated at 100° C.
stirringwith stirring for 6 hours
distillationFinally, the solvent was distilled off
customthe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-5571cc195a014f988851efc84784dfe3
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05441967

Reaction notes

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