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

HRID 392411Notes

Reaction equation

HRID 392411 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[C:16]1([O:23][CH3:24])[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:18]>>[CH3:24][O:23][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[O:18][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 460GuaiacolHCID 226638983-Bromo-N-(pyridin-3-ylmethyl)aniline

Product 1

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

Procedure

Using the method of Example 342 using N-(3-bromophenyl)pyridin-3-ylmethylamine and guaiacol (Aldrich) and purifying via preparative HPLC eluting with 1:1 DCM/ethyl acetate gave N-(3-(2-Methoxyphenoxy)phenyl) pyrid-3-ylmethylamine. Anal Calcd for C19H18N2O2.0.5H2O: C, 72.36; H, 6.07; N, 8.88. Found: C, 72.43; H, 5.80; N, 8.96. MS found 307.2 [M+H]+

Workup

  1. custompurifying via preparative HPLC
  2. washeluting with 1:1 DCM/ethyl acetate

Sources & evidence

ORD record
ord-14664bfda2b44c47ba90ad802b07d5d8
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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