2-(3-Aminophenyl)ethan-1-ol → 3-{2-[6-(4-Fluoro-phenyl)-pyridin-2-ylmethoxy]-ethyl}-phenyl amine

HRID 585175Notes

Reaction equation

HRID 585175 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:4]=1.[OH:16][CH2:17][CH2:18][C:19]1[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=1>>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[N:4]=[C:3]([CH2:2][O:16][CH2:17][CH2:18][C:19]3[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=3)[CH:8]=[CH:7][CH:6]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 149389872-(3-Aminophenyl)ethan-1-olHCID 223401212-(Chloromethyl)-6-(4-fluorophenyl)pyridine

Product 1

HCID 223401083-{2-[6-(4-Fluoro-phenyl)-pyridin-2-ylmethoxy]-ethyl}-phenyl amine

Procedure

Using a similar procedure to step 1 of Example 1 222 mg (1 mmol) of the product of step 3 above was reacted with 137 mg (1 mmol) of 3-(2-hydroxy ethyl)phenyl amine. After purification on silica with 40% ethyl acetate:hexane elution, recovered 0.21 g (65%) of an oil. NMR (200 MHz, CDCl3) δ 8.11 (m, 2H, ArH), 7.79 (m, 2H, ArH), 7.18-7.38 (m, 6H, ArH), 7.08 (d, J=8 Hz, 1H, ArH), 4.63 (s, 2H, OCH2), 4.53 (bs, 2H, NH2), 3.78 (t, J=7 Hz, 2H, OCH2), 2.92 (t, J=7 Hz, 2H, ArCH2).

Workup

  1. customAfter purification on silica with 40% ethyl acetate
  2. washhexane elution
  3. customrecovered 0.21 g (65%) of an oil

Sources & evidence

ORD record
ord-271602f65a6e43deb715f6b4206961b5
Source dataset
uspto-grants-2005_08
Patent number
US06930131B2

Reaction notes

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