Sodium borohydride → HCID 23338998, compound

HRID 28140Notes

Reaction equation

HRID 28140 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][C:7](=[N:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)[CH3:3].[BH4-].[Na+]>CO>[CH3:3][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)[CH3:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23339073HCID 23339073, compound

Product 1

HCID 23338998HCID 23338998, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and warmed (30°-40° C.) solution of 72 parts of N-[1-(1-methylethyl)-4-piperidinylidene]-benzenamine in 480 parts of methanol are added potionwise 20 parts of sodium borohydride. Upon completion, stirring is continued overnight at at room temperature. The reaction mixture is evaporated and the residue is dissolved in water. The solution is extracted with 4-methyl-2-pentanone. The extract is washed with water and acidified with a diluted hydrochloric acid solution. The aqueous acid phase is alkalized with a diluted sodium hydroxide solution till pH 9 and the product is extracted with 4-methyl-2-pentanone. The extract is washed with water, dried, filtered and evapoarated. The residue is distilled (bp. 135-140° C. at 0.2 mm. pressure) and the distillate is crystallized from petroleumether, yielding 21 parts of 1-(1-methylethyl)-N-phenyl-4-piperidinamine; mp. 69.3° C.

Workup

  1. stirringUpon completion, stirring
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in water
  4. extractionThe solution is extracted with 4-methyl-2-pentanone
  5. washThe extract is washed with water
  6. extractionthe product is extracted with 4-methyl-2-pentanone
  7. washThe extract is washed with water
  8. customdried
  9. filtrationfiltered
  10. distillationThe residue is distilled (bp. 135-140° C. at 0.2 mm. pressure)
  11. customthe distillate is crystallized from petroleumether

Sources & evidence

ORD record
ord-1ff25e688fc64cdaac4a8e2210b467cd
Source dataset
uspto-grants-1980_09
Patent number
US04225606

Reaction notes

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