1-(2-Hydroxyethyl)piperazine → 2-Acetyl-4-[4-(2-hydroxyethyl)piperazin-1-yl-methyl]phenol

HRID 23935Notes

Reaction equation

HRID 23935 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:10]([C:13]1[CH:18]=[C:17]([CH2:19]Cl)[CH:16]=[CH:15][C:14]=1[OH:21])(=[O:12])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[C:10]([C:13]1[CH:18]=[C:17]([CH2:19][N:4]2[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][OH:9])[CH2:2][CH2:3]2)[CH:16]=[CH:15][C:14]=1[OH:21])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 10340Sodium CarbonateHCID 22557013HCID 22557013, compound

Product 1

HCID 98604522-Acetyl-4-[4-(2-hydroxyethyl)piperazin-1-yl-methyl]phenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Piperazin-1-yl-ethanol (260 mg, 2 mmol) and 2-acetyl-4-chloromethyl phenol (368 mg, 2 mmol) were stirred in chloroform at room temperature. Sodium carbonate (106 mg, 1 mmol) was added and the reaction mixture was stirred overnight. The solid was filtered off and the organic layer washed with water followed by brine, dried over sodium sulfate, filtered and evaporated to obtain the crude product, which was crystallized from ethyl acetate-hexane to receive the title product as yellowish-white crystals (400 mg 72%), mp=72-75° C. C15H22N2O3 requires: N 10.06 found: N 9.70.

Workup

  1. filtrationThe solid was filtered off
  2. washthe organic layer washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e828fdfd60584281beebf8637b621e3b
Source dataset
uspto-grants-2005_02
Patent number
US06855711B1

Reaction notes

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