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

HRID 703845

反応式

HRID 703845 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0652fd7776f24f57a4347f8fc28f0b94
出典データセット
uspto-grants-1991_01
特許番号
US04985446

関連ノート

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