Phenyl glycidyl ether → 1-[[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-3-phenoxy-2-propanol

HRID 728818Notes

Reaction equation

HRID 728818 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[N:12]1([C:17]2[CH:33]=[CH:32][C:20]([O:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:19][CH:18]=2)[CH:16]=[CH:15][N:14]=[CH:13]1>CO>[N:12]1([C:17]2[CH:18]=[CH:19][C:20]([O:21][CH2:22][CH2:23][N:24]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:2][CH:3]([OH:1])[CH2:4][O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:32][CH:33]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 145556252-[4-(1H-imidazol-1-yl)phenoxy]-N-(phenylmethyl)ethanamine

Product 1

HCID 539690031-[[2-[4-(1H-Imidazol-1-yl)phenoxy]ethyl](phenylmethyl)amino]-3-phenoxy-2-propanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.2 mL (23.9 mmol) 1,2-epoxy-3-phenoxypropane in 20 mL MeOH, add 6.99 g (23.9 mmol) 2-[4-(1H-imidazol-1-yl)phenoxy]-N-(phenylmethyl)ethanamine as the free base described above. Stir at room temperature under a nitrogen atmosphere. Follow the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol, 9:1). At the completion of the reaction, evaporate the solvents. The resulting oil is chromatographed on a silica gel column using (petroleum ether :acetone, 8:2). Collect the appropriate fractions and remove the solvents to give the title compound.

Workup

  1. customthe progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol, 9:1)
  2. customAt the completion of the reaction
  3. customevaporate the solvents
  4. customThe resulting oil is chromatographed on a silica gel column
  5. customCollect the appropriate fractions
  6. customremove the solvents

Sources & evidence

ORD record
ord-805814fc04c94a7d95771dd0eb51dd3f
Source dataset
uspto-grants-1991_09
Patent number
US05051423

Reaction notes

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