3-Pyridinecarboxaldehyde → N-[4-(Tetradecyloxy)phenyl]-3-pyridinemethanamine

HRID 1728861Notes

Reaction equation

HRID 1728861 reaction equation
[CH2:1]([O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl.CO.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=O)[CH:27]=1.C([BH3-])#N.[Na+].[OH-].[K+]>O.CO>[CH2:1]([O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][CH2:32][C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 5

HCID 103713-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 191002p-(n-Tetradecyloxy)phenylamineHCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanol

Product 1

HCID 19015436N-[4-(Tetradecyloxy)phenyl]-3-pyridinemethanamineYield 76.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a room temperature slurry of 7.26 g of product from Example 82, 60 ml of methyl alcohol and 9.5 ml of 5N hydrochloric acid/methanol is added, dropwise, 2.55 g of 3-pyridinecarboxaldehyde. After 10 minutes, a total of 1.64 g of sodium cyanoborohydride is very carefully added in 3 separate portions over 1.5 hours. The initial reaction is vigorous. The reaction mixture is stirred at room temperature for 68 hours, diluted with water, made basic with potassium hydroxide and extracted with methylene chloride. The methylene chloride extract is washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 90% ethyl acetate/hexane) to give 7.2 g of the desired product as colorless crystals.

Workup

  1. customseparate portions over 1.5 hours
  2. customThe initial reaction
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washis washed with saturated sodium chloride
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (silica gel: 90% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-42263e84a1cf4a98bdd07dc05bf21934
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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