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

HRID 28125Notes

Reaction equation

HRID 28125 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 IN 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; mp. 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 IN and
  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-6ec1545350424b409648c95f9caadd8d
Source dataset
uspto-grants-1980_09
Patent number
US04225606

Reaction notes

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