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

HRID 1973776Notes

Reaction equation

HRID 1973776 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

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 2h. 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.

Workup

  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 ether
  16. washthe latter is washed with water
  17. customdried
  18. customevaporated

Sources & evidence

ORD record
ord-a0084b892e1042968e8f1306e4639fc0
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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