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

HRID 1448274
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HRID 1448274 반응식
[NH:1]([C:8]1([C:21](OCC)=[O:22])[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1C=CC=CC=1>[NH:1]([C:8]1([CH2:21][OH:22])[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매3회

실험 절차

To a stirred and refluxing solution of 101.4 parts of ethyl 4-anilino-1-benzyl-4-piperidinecarboxylate in 640 parts of dry benzene is added dropwise a solution of 172 parts of sodium dihydro-bis(2-methoxyethoxy)aluminate 70% solution 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 ether. 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 ether, the latter is washed with water, dried and evaporated, yielding 4-anilino-1-benzyl-4-piperidinemethanol as an oily residue.

후처리

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

출처 및 근거

ORD 기록
ord-c450ab8fc0c6430b9f2052a85ec2ac63
출처 데이터셋
uspto-grants-1979_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04179569

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