Sodium Hydroxide → 1-Benzyl-4-(phenylamino)piperidine-4-methanol

HRID 236774ノート

反応式

HRID 236774 の反応式
[C:1]1([NH:7][C:8]2([C:21](OCC)=[O:22])[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1C=CC=CC=1>[C:1]1([NH:7][C:8]2([CH2:21][OH:22])[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 3017395Ethyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate

生成物 1

HCID 30172301-Benzyl-4-(phenylamino)piperidine-4-methanol

試薬・触媒・溶媒 1

HCID 241Benzene溶媒3 回

実験手順

To a stirred and refluxing solution of 101.4 parts of ethyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate in 640 parts of dry benzene is added dropwise a solution of 172 parts of a sodium dihydro-bis(2-methoxyethoxy)aluminate 70% in benzene, in 160 parts of dry benzene. Upon completion, stirring is continued for 2 h. 30 at 80° C. The reaction mixture is cooled, poured onto ice-water, alkalized with sodium hydroxide solution and the product is extracted with benzene. The extract is washed twice with water, dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanol and 1,1'-oxybisethane. The salt is filtered off, boiled in 2-propanol and after cooling, the product is filtered off. It is boiled once more in acetonitrile and the salt is filtered off again after cooling. The free base is liberated in the conventional manner. After extraction with 1,1'-oxybisethane, the latter is washed with water, dried and evaporated, yielding 56.6 parts of 4-(phenylamino)-1-(phenylmethyl)-4-piperidinemethanol as an oily residue.

後処理

  1. stirringUpon completion, stirring
  2. customat 80° C
  3. temperatureThe reaction mixture is cooled
  4. additionpoured onto ice-water
  5. extractionthe product is extracted with benzene
  6. washThe extract is washed twice with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. filtrationThe salt is filtered off
  11. temperatureafter cooling
  12. filtrationthe product is filtered off
  13. filtrationthe salt is filtered off again
  14. temperatureafter cooling
  15. extractionAfter extraction with 1,1'-oxybisethane
  16. washthe latter is washed with water
  17. customdried
  18. customevaporated

出典と根拠

ORDレコード
ord-c1ab41b11bf54295a4e7e3c5f9128a36
出典データセット
uspto-grants-1979_06
特許番号
US04157393

反応ノート

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