Hydrochloric Acid → 4-Phenyl-4-piperidinocyclohexanone

HRID 1462516ノート

反応式

HRID 1462516 の反応式
Cl.C1[O:18][C:5]2([CH2:10][CH2:9][C:8]([NH2:17])([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)OC1.I[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]I.C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC)C.O.C(O)C>[C:11]1([C:8]2([N:17]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:7][CH2:6][C:5](=[O:18])[CH2:10][CH2:9]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

8

反応物 4

HCID 313Hydrochloric Acid2 回HCID 11430Potassium CarbonateHCID 123541,5-DiiodopentaneHCID 85930704HCID 85930704、化合物

生成物 1

HCID 133067564-Phenyl-4-piperidinocyclohexanone収率 61%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒4 回

実験手順

A reaction mixture consisting of the free base from 2.88 gm. (0.011 mole) of 4-amino-4-phenylcyclohexanone ethylene ketal hydrochloride (prepared in Example 32, above), 3.47 gm. 1,5-diiodopentane 2.95 gm. potassium carbonate and 25 ml. ethanol is heated at the reflux temperature, with stirring, for eighteen (18) hours. After cooling and removing most of the liquid and voltiles by evaporation under reduced pressure, the residue thus obtained is dispersed in a mixture of 100 ml. of diethyl ether and 10 ml. of water. The ether layer is allowed to separate and is recovered. It is washed with water and with brine, before removing the ether by evaporation under reduced pressure. The residue thus obtained is dissolved in diethyl ether and an amount of 3 N hydrogen chloride in diethyl ether is added so as to form the hydrochloride acid addition salt which precipitates. The salt is collected on a filter and then recrystallized from a mixture of methylene chloride and ethyl acetate. There is thus obtained 2.26 gm. (61% yield) of 4-phenyl-4-(1-piperidinyl)cyclohexanone, ethylene ketal hydrochloride having a melting range from 228° to 231° C. An analytical sample has a melting point at 234° to 235.5° C.

後処理

  1. temperatureAfter cooling
  2. customremoving most of the liquid and voltiles by evaporation under reduced pressure
  3. customthe residue thus obtained
  4. additionis dispersed in a mixture of 100 ml
  5. customto separate
  6. customis recovered
  7. washIt is washed with water and with brine
  8. custombefore removing the ether
  9. customby evaporation under reduced pressure
  10. customThe residue thus obtained
  11. customto form
  12. customprecipitates
  13. customThe salt is collected on
  14. filtrationa filter
  15. customrecrystallized from a mixture of methylene chloride and ethyl acetate

出典と根拠

ORDレコード
ord-dc4daf26cb6649e1993d1511cf85a363
出典データセット
uspto-grants-1984_07
特許番号
US04460604

反応ノート

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