Acetone → (-)-trans-1(2-Cyanoethyl)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-piperidine hydrochloride

HRID 247817

반응식

HRID 247817 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][C:29]#[N:30].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(O)C.C(OCC)C>[ClH:1].[C:29]([CH2:28][CH2:27][N:12]1[CH2:13][CH2:14][C@@H:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[C@H:10]([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)[CH2:11]1)#[N:30]

참가 물질

7

반응물 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 170203-BromopropionitrileHCID 62878Paroxetine Hydrochloride

생성물 1

HCID 67638429(-)-trans-1(2-Cyanoethyl)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-piperidine hydrochloride

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

1 g of (-)-trans-4-(4-fluorophenyl)-3-(3,4-methylene dioxyphenoxymethyl)-piperidine hydrochloride in 50 ml 99.9% ethanol was mixed with 3-bromopropionitrile (7 ml) and 2 g potassium carbonate. The mixture was refluxed for 70 h. After cooling 25 ml acetone and 25 ml diethylether were added, the precipitate filtered off, and the filtrate evaporated in vacuo. The residue was extracted with 1N NaOH/ether, the ether layer dried (MgSO4) and evaporated to dryness. The residue was dissolved in acetone and excess conc. HCl was added. Subsequent evaporation gave a hard glass, which was purified on a silica gel column using 99.5% ethanol as eluent. The title compound was isolated, and its structure confirmed by the IR and NMR data. M.p. 156° C.

후처리

  1. temperatureThe mixture was refluxed for 70 h
  2. additionwere added
  3. filtrationthe precipitate filtered off
  4. customthe filtrate evaporated in vacuo
  5. extractionThe residue was extracted with 1N NaOH/ether
  6. dry with materialthe ether layer dried (MgSO4)
  7. customevaporated to dryness
  8. dissolutionThe residue was dissolved in acetone
  9. additionexcess conc. HCl was added
  10. customSubsequent evaporation
  11. customgave a hard glass, which
  12. customwas purified on a silica gel column

출처 및 근거

ORD 기록
ord-bc58671cd8f744e6be94e6e319b23dc1
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208232

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