Sodium borohydride → HCID 12875605, compound

HRID 2286687Notes

Reaction equation

HRID 2286687 reaction equation
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:8]2[CH2:13][CH2:12][CH:11]([N:14]=[CH:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:22]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12875558HCID 12875558, compound

Product 1

HCID 12875605HCID 12875605, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3.55 parts of 1-(diphenylmethyl)-N-[(4-pyridyl)methylene]-4-piperidinamine in 150 parts by volume of ethanol, stirred at room temperature, is treated with 1 part of sodium borohydride. The resultant reaction mixture is stirred at room temperature for about three hours, then evaporated to dryness in vacuo. The residue is partitioned between 100 parts by volume of water and 100 parts by volume of chloroform and the layers separated. The aqueous layer is extracted with additional 100 parts by volume of chloroform and the chloroform layers combined. The combined chloroform fraction is washed with 150 parts by volume of water, dried over anhydrous sodium sulfate and evaporated to dryness to yield 1-(diphenylmethyl)-N-[(4-pyridyl)methyl]-4-piperidinamine which melts, after recrystallization from n-hexane, at about 138°-162° C. This compound is represented by the following structural formula. ##STR37##

Workup

  1. customThe resultant reaction mixture
  2. stirringis stirred at room temperature for about three hours
  3. customevaporated to dryness in vacuo
  4. customThe residue is partitioned between 100 parts by volume of water and 100 parts by volume of chloroform
  5. customthe layers separated
  6. extractionThe aqueous layer is extracted with additional 100 parts by volume of chloroform
  7. washThe combined chloroform fraction is washed with 150 parts by volume of water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-9beaba41ae614f838097f5cde4b86df4
Source dataset
uspto-grants-1981_05
Patent number
US04267318

Reaction notes

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