Aniline → 1-Anilino-3-[4-(diphenylmethyl)piperazin-1-yl]propan-2-ol

HRID 274902Notes

Reaction equation

HRID 274902 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[O:17][CH2:16]3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH:15]([OH:17])[CH2:16][NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 102447781-(Diphenylmethyl)-4-[(oxiran-2-yl)methyl]piperazine

Product 1

HCID 30726961-Anilino-3-[4-(diphenylmethyl)piperazin-1-yl]propan-2-olYield 49.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.08 g (0.01 mol) of 1-(diphenylmethyl)-4-(2,3-epoxypropyl)piperazine and 0.93 g (0.01 mol) of aniline were refluxed with heating together with 200 ml of DMF for 21 hours in the presence of a catalytic amount of an alkali such as potassium carbonate. DMF was distilled off under reduced pressure, and a residue was extracted with ethyl acetate. After washing with water and drying, the ethyl acetate was distilled off under reduced pressure to obtain 4 g of a crude subject compound of a viscous liquid. The obtained compound was refined by flush chromatography and fractional thin-layer chromatography by using solvent mixtures of ethyl acetate--methanol and methylene chloride--methanol respectively to obtain 2 g of the subject compound as yellow crystals.

Workup

  1. distillationDMF was distilled off under reduced pressure
  2. extractiona residue was extracted with ethyl acetate
  3. washAfter washing with water
  4. customdrying
  5. distillationthe ethyl acetate was distilled off under reduced pressure
  6. customto obtain 4 g of a crude
  7. customby flush chromatography and fractional thin-layer chromatography

Sources & evidence

ORD record
ord-a5c1cb5a219c4edf9fe9b2fb8110dce7
Source dataset
uspto-grants-1995_02
Patent number
US05391552

Reaction notes

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