3-Pyridinecarboxaldehyde → N-((4-phenoxy)phenylethyl)pyridine-3-methylamine

HRID 392391Notes

Reaction equation

HRID 392391 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[O:9]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][NH2:22])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+]>CO>[O:9]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][CH2:21][NH:22][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:23][CH:24]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 1455354-PhenoxyphenethylamineHCID 4311764Sodium borohydride

Product 1

HCID 69881198N-((4-phenoxy)phenylethyl)pyridine-3-methylamineYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of pyridine-3-carboxaldehyde (322 mg, 3.0 mmol) and 4-phenoxyphenethylamine (747 mg, 3.5 mmol) in reagent grade methanol (5 mL) under nitrogen was refluxed for 2 h, then cooled to 5° C. (ice bath), and diluted with more methanol (5 mL). Sodium borohydride (0.23 g, 6 mmol) was added, and the mixture was slowly allowed to reach room temperature and stirred at room temperature overnight (18 h). The mixture was concentrated in vacuo, taken up in dichloromethane, and filtered. The filtrate was concentrated in vacuo and chromatographed on silica gel (eluted with 7% methanol/dichloromethane) to afford N-((4-phenoxy)phenylethyl)pyridine-3-methylamine (863 mg, 94%).

Workup

  1. customto reach room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customchromatographed on silica gel (eluted with 7% methanol/dichloromethane)

Sources & evidence

ORD record
ord-78334a7dc6754ff8b9a39cb558175067
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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