Sodium borohydride → HCID 12875598, compound

HRID 2286685Notes

Reaction equation

HRID 2286685 reaction equation
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:8]2[CH2:13][CH2:12][CH:11]([N:14]=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)C>[C:23]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=3)[CH2:10][CH2:9]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12875557HCID 12875557, compound

Product 1

HCID 12875598HCID 12875598, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.55 parts of 1-(diphenylmethyl)-N-[(6-methyl-2-pyridyl)methylene]-4-piperidinamine, 1.9 part of sodium borohydride and 250 parts by volume of ethanol is stirred at room temperature for about two hours. The reaction mixture is evaporated to dryness in vacuo, the residue partitioned between 200 parts by volume of water and 150 parts by volume of methylene chloride and the layers separated. The aqueous layer is extracted with additional 125 parts by volume of methylene chloride. The methylene chloride fractions are combined, washed with 200 parts by volume of water, dried over anhydrous sodium sulfate, filtered and evaporated to dryness in vacuo to yield, as a yellow oil, 1-(diphenylmethyl)-N-[(6-methyl-2-pyridyl)methyl]-4-piperidinamine. This compound has the following formula ##STR35##

Workup

  1. customThe reaction mixture is evaporated to dryness in vacuo
  2. customthe residue partitioned between 200 parts by volume of water and 150 parts by volume of methylene chloride
  3. customthe layers separated
  4. extractionThe aqueous layer is extracted with additional 125 parts by volume of methylene chloride
  5. washwashed with 200 parts by volume of water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5d693a17e53742498b5bf27b1fe2b642
Source dataset
uspto-grants-1981_05
Patent number
US04267318

Reaction notes

Loading…