Sodium borohydride → Ethyl 4-[(4-chlorophenyl)amino]piperidine-1-carboxylate

HRID 236739Notes

Reaction equation

HRID 236739 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14665236Ethyl 4-[(4-chlorophenyl)imino]-1-piperidinecarboxylate

Product 1

HCID 2846949Ethyl 4-[(4-chlorophenyl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a warm solution of 192 parts of ethyl 4-[(4-chlorophenyl)imino]-1-piperidinecarboxylate in 560 parts of methanol is added portionwise 23.5 parts of sodium borohydride at 50° C. and over a period of one hour. After the addition is complete, the mixture is stirred at the same temperature for 2 hours. The methanol is evaporated. The solid residue is heated with ±600 parts of water and the product is extracted with benzene. The extract is dried over magnesium sulfate and evaporated. The oily residue solidifies on treating with 2,2'-oxybispropane. The solid is filtered off and dried, yielding 122 parts of ethyl 4-[(4-chlorophenyl)amino]-1-piperidinecarboxylate; mp. 115°-118° C.

Workup

  1. additionAfter the addition
  2. customThe methanol is evaporated
  3. temperatureThe solid residue is heated with ±600 parts of water
  4. extractionthe product is extracted with benzene
  5. dry with materialThe extract is dried over magnesium sulfate
  6. customevaporated
  7. additionon treating with 2,2'-oxybispropane
  8. filtrationThe solid is filtered off
  9. customdried

Sources & evidence

ORD record
ord-62fc8a1be4714589bd468a9c8c75c81d
Source dataset
uspto-grants-1979_06
Patent number
US04157393

Reaction notes

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