3-Pyridinecarboxaldehyde → N-(3-(2-Methoxyphenoxy)phenyl) pyrid-3-ylmethylamine

HRID 392389Notes

Reaction equation

HRID 392389 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([NH:9][CH2:23][C:19]2[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 226635563-(2-methoxyphenoxy)Benzenamine

Product 1

HCID 22663896N-(3-(2-Methoxyphenoxy)phenyl) pyrid-3-ylmethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 3-(2-methoxyphenoxy)aniline (269 mg, 1.25 mmol) and pyridine-3-carboxaldehyde (107 mg, 1.00 mmol) was refluxed in methanol (2.5 mL) for 2 h, then cooled on an ice bath to 5° C. Sodium borohydride (95 mg, 2.5 mmol) was added and the mixture was warmed to room temperature, stirred for 2 h, concentrated in vacuo, and taken up in dichloromethane. The resultant suspension was filtered, the filtrate concentrated in vacuo, and the residue chromatographed on silica gel (eluted with 2% methanol/dichloromethane) to give N-(3-(2-methoxyphenoxy)phenyl)pyrid-3-ylmethylamine.

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. concentrationconcentrated in vacuo
  3. filtrationThe resultant suspension was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customthe residue chromatographed on silica gel (eluted with 2% methanol/dichloromethane)

Sources & evidence

ORD record
ord-0572584e64a542aeb690faa8bf3f0df4
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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