(4-Aminophenoxy)benzene → HCID 4712132, compound

HRID 392406Notes

Reaction equation

HRID 392406 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=1>>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:12][CH2:21][C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8764(4-Aminophenoxy)benzeneHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 4712132HCID 4712132, compound

Procedure

Using the method of Example 343 using 4-phenoxyaniline (Aldrich) and 3-pyridinecarboxaldehyde (Aldrich) and purifying via preparative HPLC eluting with 95:5 to 60:40 DCM/ethyl acetate gave N-(4-phenoxypheny)pyridin-3-ylmethylamine. Anal Calcd for C18H16N2O: C, 78.24; H, 5.84; N, 10.14. Found: C, 78.19; H, 5.67; N, 10.03. 1H NMR (400 MHz, DMSO) 4.00 (1H, bt), 4.35 (2H, d, J=5.1 Hz), 6.62 (2H, m), 6.89-6.93 (4H, m), 6.99-7.03 (1H, m), 7.25-7.30 (3H, m), 7.71 (1H, m), 8.54 (1H, dd, J=1.8, 4.8 Hz), 8.64 (1H, d, J=1.8 Hz) MS found 277.0 [M+H]+

Workup

  1. custompurifying via preparative HPLC
  2. washeluting with 95:5 to 60:40 DCM/ethyl acetate

Sources & evidence

ORD record
ord-96542f309f6e4789af13367cc650bb1c
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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