Sodium Carbonate → methyl 4-[N-(4-chlorophenyl)acetyl-N-phenylamino]-1-(1-methylethyl)-4-piperidinecarboxylate ethanedioate

HRID 28153

反応式

HRID 28153 の反応式
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)[CH3:3].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[O:30])=[CH:24][CH:23]=1.[C:32](=[O:35])([O-:34])[O-].[Na+].[Na+].[OH-].[Na+]>CC1C=CC=CC=1C>[C:10]([OH:12])(=[O:11])[C:32]([OH:34])=[O:35].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([N:14]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6]2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:30])=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 906924-Chlorophenylacetyl chlorideHCID 20382310Methyl 1-(1-methylethyl)-4-(phenylamino)-4-piperidinecarboxylate

生成物 1

HCID 86736171methyl 4-[N-(4-chlorophenyl)acetyl-N-phenylamino]-1-(1-methylethyl)-4-piperidinecarboxylate ethanedioate収率 48%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A mixture of 5 parts of methyl 1-(1-methylethyl)-4-(phenylamino)-4-piperidinecarboxylate, 24 parts of 4-chlorobenzeneacetyl chloride, 4 parts of sodium carbonate and 180 parts of dimethylbenzene is stirred and refluxed for 32 hours. The reaction mixture is cooled, washed with a diluted sodium hydroxide solution and extracted with a diluted hydrochloric acid solution:three layers are obtained. The oil and the aqueous phase are combined and alkalized with a diluted sodium hydroxide solution. The product is extracted with 4-methyl-2-pentanone. The extract is washed with water, dried, filtered and evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and crystallized from a mixture of 2-propanol and 2,2'-oxybispropane, yielding 5 parts (48%) of methyl 4-[N-(4-chlorophenyl)acetyl-N-phenylamino]-1-(1-methylethyl)-4-piperidinecarboxylate ethanedioate; mp. 154.2° C.

後処理

  1. temperaturerefluxed for 32 hours
  2. temperatureThe reaction mixture is cooled
  3. washwashed with a diluted sodium hydroxide solution
  4. extractionextracted with a diluted hydrochloric acid solution
  5. customthree layers are obtained
  6. extractionThe product is extracted with 4-methyl-2-pentanone
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. filtrationThe salt is filtered off
  12. customcrystallized from a mixture of 2-propanol and 2,2'-oxybispropane

出典と根拠

ORDレコード
ord-76abe538d8274d7185ba49391459a948
出典データセット
uspto-grants-1980_09
特許番号
US04225606

関連ノート

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