Water → 2-[4-(1H-imidazol-1-yl)phenoxy]-N-(phenylmethyl)ethanamine

HRID 232322

Reaction equation

HRID 232322 reaction equation
[H-].[Na+].[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.Cl.[CH2:16]([NH:23][CH2:24][CH2:25]Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O.C(Cl)Cl.CO>[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:25][CH2:24][NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 823151-(p-Hydroxyphenyl)imidazoleHCID 13054189Benzenemethanamine, N-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a chilled suspension of 39.5 g (0.823 mol) 50% sodium hydride in 500 mL dimethylformamide add 37.32 g (0.233 mol) 4-(1H imidazol-1-yl)phenol. When the addition is complete, stir the reaction mixture at room temperature until gas evolution ceases. After this time, chill the reaction mixture below 0° C. and slowly add 60.22 g (0.292 mol) N-benzyl(2-chloro)ethylamine hydrochloride. When the addition is complete, heat the reaction mixture to 65° C. Follow the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol) (9:1). At the completion of the reaction, add 20 mL water to the cooled mixture. Filter the slats and remove the solvents in vacuo to obtain an oil. Column chromatograph the oil on silica gel using methylene chloride+methanol (1+99→1+19) as eluent. Collect the appropriate fractions and remove the solvents to obtain the title compound as the free base. Dissolve the free base in excess methanolic HCl solution and remove the solvent in vacuo to provide the title compound.

Workup

  1. additionWhen the addition
  2. additionWhen the addition
  3. temperatureheat the reaction mixture to 65° C
  4. customthe progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol) (9:1)
  5. customAt the completion of the reaction
  6. filtrationFilter the slats
  7. customremove the solvents in vacuo
  8. customto obtain an oil
  9. customCollect the appropriate fractions
  10. customremove the solvents

Sources & evidence

ORD record
ord-9ce88200164d4d8bb79a0337f4665721
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Linked notes

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