Acetone → (-)-trans-4-(-4-Fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-pentylpiperidine hydrochloride

HRID 2352543Notes

Reaction equation

HRID 2352543 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]2[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)=[CH:5][CH:4]=1.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(O)C.C(OCC)C>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][N:12]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:11][C@H:10]2[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 62878Paroxetine Hydrochloride

Product 1

HCID 66923321(-)-trans-4-(-4-Fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-pentylpiperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

10 g of (-)-trans-4-(-4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-piperidine hydrochloride in 250 ml 99.9% ethanol was mixed with 50 ml 1-bromopentane and 20 g potassium carbonate. The mixture was refluxed for 3 hours and was subsequently cooled to room temperature. 25 ml acetone and 25 ml diethylether was added to the solution. The precipitate was filtered off and the filtrate was evaporated in vacuo. 20 ml 4N NaOH was added to the residue, and the resulting mixture was extracted 3 times with diethyl ether. The combined ether phases were dried over potassium carbonate, filtered, the filtrate was acidified with conc. hydrochloric acid to pH 2, and the filtrate was evaporated in vacuo. The resulting oil was dissolved in acetone and crystals precipitated by addition of ether and after cooling at 4° C. over night. The title compound was filtered off and dried giving 10.1 g of the title compound. M.p. 153.6° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was evaporated in vacuo
  4. addition20 ml 4N NaOH was added to the residue
  5. extractionthe resulting mixture was extracted 3 times with diethyl ether
  6. dry with materialThe combined ether phases were dried over potassium carbonate
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo
  9. dissolutionThe resulting oil was dissolved in acetone
  10. customcrystals precipitated by addition of ether
  11. temperatureafter cooling at 4° C. over night
  12. filtrationThe title compound was filtered off
  13. customdried

Sources & evidence

ORD record
ord-7bf994e45c424b1d96d116867594911a
Source dataset
uspto-grants-1989_10
Patent number
US04877799

Reaction notes

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