Diethyl Ether → 8-Methyl-1-naphthyl 4-piperidyl ketone hydrochloride

HRID 1389870

反応式

HRID 1389870 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:12])[CH:5]=[CH:4][CH:3]=1.[Mg].C([N:17]1[CH2:22][CH2:21][CH:20]([C:23]#N)[CH2:19][CH2:18]1)(=O)C.[Cl-:25].[NH4+].C([O:29]CC)C>O1CCCC1>[ClH:25].[NH:17]1[CH2:18][CH2:19][CH:20]([C:23]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[CH3:12])[CH:5]=[CH:4][CH:3]=2)=[O:29])[CH2:21][CH2:22]1

参加物

7

反応物 5

HCID 3283Diethyl Ether2 回HCID 25517Ammonium ChlorideHCID 27562861-Acetylpiperidine-4-carbonitrileHCID 42509491-Bromo-8-methylnaphthaleneHCID 5462224Magnesium

生成物 1

HCID 202955708-Methyl-1-naphthyl 4-piperidyl ketone hydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 10.0 g (45 mmoles) of 1-bromo-8-methylnaphthalene in 5 ml of ethyl ether is added gradually to a stirred mixture of 1.2 g (50 mmoles) of magnesium in 30 ml of anhydrous ether. The mixture is stirred at reflux for 1 hour and a solution of 6.0 g (43 mmoles) of 1-acetyl-4-piperidinecarbonitrile in 10 ml of tetrahydrofuran slowly added. The mixture is allowed to stir for 16 hours, an excess of saturated aqueous ammonium chloride solution added and the mixture heated on a steam bath for 3 hours. After cooling, the mixtures is extracted with toluene and the organic phase dried over MgSO4, filtered and concentrated in vacuo. The residue is dissolved in 20 ml of ethanol and made basic with sodium hydroxide and the solution extracted into toluene. Dry hydrogen chloride is bubbled through the organic phase to yield 8-methyl-1-naphthyl 4-piperidyl ketone hydrochloride.

後処理

  1. temperatureat reflux for 1 hour
  2. stirringto stir for 16 hours
  3. temperaturethe mixture heated on a steam bath for 3 hours
  4. temperatureAfter cooling
  5. extractionthe mixtures is extracted with toluene
  6. dry with materialthe organic phase dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue is dissolved in 20 ml of ethanol
  10. extractionthe solution extracted into toluene
  11. customDry hydrogen chloride is bubbled through the organic phase

出典と根拠

ORDレコード
ord-80c70c83a58a47b79c299725578eccaf
出典データセット
uspto-grants-1981_01
特許番号
US04246268

関連ノート

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