Sodium borohydride → N-[1-(phenylmethyl)-4-piperidinyl]-3-pyridinamine

HRID 26731Notes

Reaction equation

HRID 26731 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=[N:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10706822N-[1-(phenylmethyl)-4-piperidinylidene]-3-pyridinamine

Product 1

HCID 10706957N-[1-(phenylmethyl)-4-piperidinyl]-3-pyridinamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 27 parts of N-[1-(phenylmethyl)-4-piperidinylidene]-3-pyridinamine in 40 parts of ethanol are added portionwise 3.8 parts of sodium borohydride. After the addition is complete, the whole is heated to 50° C. The solvent is evaporated. The oily residue is dissolved in 150 parts of hydrochloric acid 1N and filtered. The filtrate is rendered alkaline with ammonium hydroxide and extracted with methylbenzene. The organic layer is dried over magnesium sulfate, filtered and evaporated. The solid residue is washed with 2,2'-oxybispropane and dried, yielding 14 parts of N-[1-(phenylmethyl)-4-piperidinyl]-3-pyridinamine; m.p. 131°-133° C.; beige, amorphous powder.

Workup

  1. additionAfter the addition
  2. customThe solvent is evaporated
  3. dissolutionThe oily residue is dissolved in 150 parts of hydrochloric acid 1N
  4. filtrationfiltered
  5. extractionextracted with methylbenzene
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. washThe solid residue is washed with 2,2'-oxybispropane
  10. customdried

Sources & evidence

ORD record
ord-b6aa8350907c43e2a1b31831c8e011fc
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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