Potassium Hydroxide → HCID 54065698, compound

HRID 1976610Notes

Reaction equation

HRID 1976610 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=O)[CH:2]=1.[C:11]1([CH2:17][CH2:18][CH2:19][NH2:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([BH3-])#N.[Na+].[OH-].[K+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][NH:20][CH2:19][CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 162593-PhenylpropylamineHCID 5003444Sodium cyanoborohydrideHCID 111054123-(Pyridin-3-yl)propanal

Product 1

HCID 54065698HCID 54065698, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of 3-(3-pyridyl)propionaldehyde (4.40 g, 32.5 mmoles) and 3-phenylpropylamine (5.30 g, 1.2 equiv.) in methanol at rt was treated with sodium cyanoborohydride (1 g, 0.5 equiv.). After 1 h at rt the mixture was further treated with solid potassium hydroxide (3.6 g, 2 equiv.) and stirring was continued for 2 h. The resulting mixture was partitioned between brine and ether. The aqueous layer was extracted with ether and the combined ether extracts were extracted with 6N HCl (3×). These aqueous extracts were basified with solid potassium hydroxide and extracted with ether (3×), dried over sodium sulfate and concentrated in vacuo. The residue was distilled under high vacuum to give the product as a colorless oil (2.44 g, 30%), b.p. ca. 162° C./0.5 mm Hg.

Workup

  1. customThe resulting mixture was partitioned between brine and ether
  2. extractionThe aqueous layer was extracted with ether
  3. extractionthe combined ether extracts were extracted with 6N HCl (3×)
  4. extractionextracted with ether (3×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was distilled under high vacuum

Sources & evidence

ORD record
ord-2dd79dc8731147449ca519baa82932f0
Source dataset
uspto-grants-2001_05
Patent number
US06228872B1

Reaction notes

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