3-(Trifluoromethyl)benzylamine → 7-[2-Hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}amino)propoxy]-3-(4-methoxyphenyl)chromen-4-one

HRID 1694660Notes

Reaction equation

HRID 1694660 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][C:14]([O:20][CH2:21][CH:22]4[CH2:24][O:23]4)=[CH:15][CH:16]=3)[O:11][CH:10]=2)=[CH:5][CH:4]=1.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31].C(N(C(C)C)CC)(C)C>C(O)C>[OH:23][CH:22]([CH2:24][NH:31][CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:27]([C:26]([F:35])([F:36])[F:25])[CH:28]=1)[CH2:21][O:20][C:14]1[CH:13]=[C:12]2[C:17]([C:18](=[O:19])[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:10][O:11]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 759623-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 86618198HCID 86618198, compound

Product 1

HCID 672791297-[2-Hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}amino)propoxy]-3-(4-methoxyphenyl)chromen-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Methoxyphenyl)-7-(oxiran-2-ylmethoxy)chromen-4-one (0.24 g, 0.74 mmol), 3-(trifluoromethyl)benzylamine (0.11 ml, 0.74 mmol) and diisopropylethylamine (0.26 g, 1.47 mmol) was stirred in ethanol (15 ml) at 78° C. overnight. The solvent was removed under reduced pressure, and the residue chromatographed on silica gel, eluting with 5% methanol/dichloromethane, followed by recrystallization from ethyl acetate/hexane to provide 7-[2-hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}amino)propoxy]-3-(4-methoxyphenyl)chromen-4-one.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue chromatographed on silica gel
  3. washeluting with 5% methanol/dichloromethane
  4. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-889b219ffe0245de8651269fddd4397a
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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