Sodium borohydride → HCID 13094167, compound

HRID 1164364Notes

Reaction equation

HRID 1164364 reaction equation
[C:1]([C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:8][CH2:7][C:6]([N:9]2[CH2:14][CH2:13][C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH2:4]1)#[N:2].[BH4-].[Na+]>C(O)C>[C:1]([C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:4][CH2:5][CH:6]([N:9]2[CH2:10][CH2:11][C:12]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:8]1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13094166HCID 13094166, compound

Product 1

HCID 13094167HCID 13094167, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 4.5 parts of ethyl 1-[4-cyano-4-(2-pyridinyl)-1-cyclohexenyl]-4-phenyl-4-piperidinecarboxylate and 80 parts of ethanol are added portionwise 0.4 parts of sodium borohydride. Upon completion, stirring is continued first overnight at room temperature and further for 30 minutes at reflux. The reaction mixture is cooled and poured onto water. The product is extracted with dichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 2 parts (35%) of ethyl 1-[4-cyano-4-(2-pyridinyl)cyclohexyl]-4-phenyl-4-piperidinecarboxylate; mp. 157.1° C.

Workup

  1. temperatureat reflux
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted with dichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-9bd39efd566e4ffdb12b28a532a07b97
Source dataset
uspto-grants-1983_01
Patent number
US04369184

Reaction notes

Loading…