Sulfuric Acid → 1-Benzyl-4-phenylpiperidine-4-carboxamide

HRID 895791

反応式

HRID 895791 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:20]#[N:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].S(=O)(=O)(O)[OH:25]>O.C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:20]([NH2:21])=[O:25])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 1118Sulfuric AcidHCID 14798Sodium Hydroxide2 回HCID 1914081-Benzyl-4-cyano-4-phenylpiperidine2 回

生成物 1

HCID 964231-Benzyl-4-phenylpiperidine-4-carboxamide収率 95%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒3 回HCID 1140Toluene溶媒2 回

反応条件

温度
60 °C

実験手順

A mixture of 3 kg of commercial 1-benzyl-4-cyano-4-phenylpiperidine, 6 l of water, 8.98 l of toluene and 1.35 kg of an aqueous 35% sodium hydroxide solution is heated under nitrogen at 60° C. and the aqueous phase is separated out by settling at this temperature. The toluene phase is dried by azeotropic distillation and the solution thus obtained containing the 1-benzyl-4-cyano-4-phenylpiperidine base is added to a mixture of 2.83 kg of 95% sulfuric acid, 1.73 kg of glacial acetic acid and 3 l of toluene. The mixture thus obtained is heated for 6 hours, the heating is then stopped, the mixture is cooled to 60° C. and 3 l of water are added at this temperature. The mixture is allowed to cool to room temperature (about 20° C.) and is then poured into 8.65 l of 30% sodium hydroxide and 6.75 l of water. The temperature rises gradually to 75° C. The phases are separated by settling while hot and the organic phase is washed with water and dried azeotropically. The toluene solution is concentrated to half its volume and then cooled gradually to 60° C. and the crystallization is initiated. The crystallization is completed by cooling to 0° C. over 2 hours. The precipitate thus obtained is filtered off, washed and dried under vacuum at 60° C. 2.68 kg of 1-benzyl-4-phenyl-4-piperidinecarboxamide are thus obtained;

後処理

  1. customthe aqueous phase is separated out
  2. dry with materialThe toluene phase is dried by azeotropic distillation
  3. customthe solution thus obtained
  4. customThe mixture thus obtained
  5. temperatureis heated for 6 hours
  6. temperaturethe mixture is cooled to 60° C.
  7. temperatureto cool to room temperature (about 20° C.)
  8. customrises gradually to 75° C
  9. customThe phases are separated
  10. washis washed with water
  11. customdried azeotropically
  12. concentrationThe toluene solution is concentrated to half its volume
  13. temperaturecooled gradually to 60° C.
  14. customthe crystallization
  15. customThe crystallization
  16. temperatureby cooling to 0° C. over 2 hours
  17. customThe precipitate thus obtained
  18. filtrationis filtered off
  19. washwashed
  20. customdried under vacuum at 60° C

出典と根拠

ORDレコード
ord-caf87a1502044bfe95fd5f63f7299f11
出典データセット
uspto-grants-2005_07
特許番号
US06916929B2

関連ノート

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