Hydrochloric Acid → 3,4-dichloro-N-(4-chlorophenyl)-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide

HRID 236768

反応式

HRID 236768 の反応式
[NH2-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29](Cl)=[O:30])[CH:24]=[CH:25][C:26]=1[Cl:27].Cl.[OH-].[Na+]>O.C1C=CC=CC=1>[Cl:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29]([N:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)[CH:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]2)=[O:30])[CH:24]=[CH:25][C:26]=1[Cl:27]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24533Sodium amideHCID 27581492-(3,4-Dichlorophenyl)acetyl chlorideHCID 3017394N-(4-Chlorophenyl)-1-isopropylpiperidin-4-amine

生成物 1

HCID 233390293,4-dichloro-N-(4-chlorophenyl)-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide

試薬・触媒・溶媒 2

HCID 241Benzene溶媒3 回HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

A suspension of 1.25 parts of sodium amide in 56 parts of benzene is stirred under nitrogen atmosphere and warmed to a temperature of 40° C. Then there is added dropwise a solution of 6 parts of N-(4-chlorophenyl)-1-(1-methylethyl)-4-piperidinamine in 56 parts of benzene. Upon completion, the whole is stirred and refluxed for 16h.45. The mixture is cooled to 25° C. and there is added a mixture of 7.8 parts of 3,4-dichlorobenzeneacetyl chloride in 88 parts of benzene. After stirring and refluxing for 2 additional hours the reaction mixture is cooled and 80 parts of water are added. The whole is acidified with a diluted hydrochloric acid solution. The aqueous acid phase is alkalized with sodium hydroxide solution and the free base is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is dissolved in a mixture of 80 parts of 1,1'-oxybisethane and 120 parts of hexane. The solution is cooled overnight at -10° C., filtered from some impurities and the filtrate is evaporated again. The residue is dissolved in 120 parts of 1,1'-oxybisethane, treated with activated charcoal, filtered and evaporated. The latter residue is crystallized from hexane at -10° C., yielding 2.2 parts of 3,4-dichloro-N-(4-chlorophenyl)-N-[1-(1-methylethyl)-4-piperidinyl]benzeneacetamide; mp. 101.7° C.

後処理

  1. stirringUpon completion, the whole is stirred
  2. temperaturerefluxed for 16h.45
  3. temperatureThe mixture is cooled to 25° C.
  4. additionthere is added
  5. stirringAfter stirring
  6. temperaturerefluxing for 2 additional hours the reaction mixture
  7. temperatureis cooled
  8. extractionthe free base is extracted with trichloromethane
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. dissolutionThe residue is dissolved in a mixture of 80 parts of 1,1'-oxybisethane and 120 parts of hexane
  13. temperatureThe solution is cooled overnight at -10° C.
  14. filtrationfiltered from some impurities
  15. customthe filtrate is evaporated again
  16. dissolutionThe residue is dissolved in 120 parts of 1,1'-oxybisethane
  17. additiontreated with activated charcoal
  18. filtrationfiltered
  19. customevaporated
  20. customThe latter residue is crystallized from hexane at -10° C.

出典と根拠

ORDレコード
ord-f0712e222c5a4850b3d6c27eac985c6b
出典データセット
uspto-grants-1979_06
特許番号
US04157393

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