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

HRID 703845

반응식

HRID 703845 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

10g of (-)-trans-4-(-4-fluorophenyl)-3-(3,4-methylenedioxy-phenoxymethyl)-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.

후처리

  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

출처 및 근거

ORD 기록
ord-0652fd7776f24f57a4347f8fc28f0b94
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04985446

연결된 노트

불러오는 중…