Ethanol → 4-Phenyl-4-(1-pyrrolidinyl)cyclohexanone

HRID 1448563ノート

反応式

HRID 1448563 の反応式
[NH2:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.Br[CH2:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+].C(O)C>O>[C:9]1([C:2]2([N:1]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:3][CH2:4][C:5](=[O:8])[CH2:6][CH2:7]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 702EthanolHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 204533024-Amino-4-phenylcyclohexan-1-one

生成物 1

HCID 133452724-Phenyl-4-(1-pyrrolidinyl)cyclohexanone収率 49%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A reaction mixture consisting of the free base from 2.69 gm. (0.01 mole) of 4-amino-4-phenylcyclohexanone, ethylene ketal hydrochloride (prepared in Example 32, above) 2.16 gm. of 1,4-dibromobutane, 2.76 gm. potassium carbonate, and 15.0 ml. ethanol is heated at the reflux temperature, with stirring, for eighteen (18) hours. The volatile components are then substantially removed by evaporation under reduced pressure, and the concentrate thus obtained diluted with water. A precipitate forms which is collected on a filter and dissolved in diethyl ether. The ether solution is treated with an equivalent of 3 N hydrogen chloride in diethyl ether. A precipitate that forms is collected on a filter and recrystallized from a mixture of methylene chloride and ethyl acetate. There is thus obtained 1.57 gm. (49% yield) of 4-phenyl-4-(1-pyrrolidinyl)cyclohexanone, ethylene ketal hydrochloride having a melting range from 238° to 239.5° C.

後処理

  1. customThe volatile components are then substantially removed by evaporation under reduced pressure
  2. concentrationthe concentrate thus
  3. customobtained
  4. customA precipitate forms which is collected on
  5. filtrationa filter
  6. dissolutiondissolved in diethyl ether
  7. additionThe ether solution is treated with an equivalent of 3 N hydrogen chloride in diethyl ether
  8. customA precipitate that forms is collected on
  9. filtrationa filter
  10. customrecrystallized from a mixture of methylene chloride and ethyl acetate

出典と根拠

ORDレコード
ord-a295188dcb8444d5bb334d20e0457c6d
出典データセット
uspto-grants-1979_12
特許番号
US04180584

反応ノート

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