Water → 4-Benzyl-1-(2-methoxyphenyl)-2-piperazinone

HRID 463721Notes

Reaction equation

HRID 463721 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[C:2]1C=CC=CC=1.C(=O)([O-])[O-:28].[Na+].[Na+].ClCC(Cl)=O.O>C(Cl)Cl>[CH2:20]([N:8]1[CH2:9][CH2:10][N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[C:2](=[O:28])[CH2:1]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 20255245N,N-dibenzyl-N'-(2-methoxyphenyl)ethylenediamine

Product 1

HCID 135605464-Benzyl-1-(2-methoxyphenyl)-2-piperazinoneYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 21.6 g of N,N-dibenzyl-N'-(2-methoxyphenyl)-ethylenediamine in 400 ml methylene chloride was added 12.9 g of sodium carbonate. To this mixture, a solution of 8.42 g of chloroacetylchloride in 100 ml methylene chloride was added dropwise over 30 minutes and stirred for 1 hour. Water (500 ml) was added, the organic phase separated, washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue (27.9 g) in a flask was immersed in a 180° oil bath and the formed benzylchloride removed by distillation. The crude material was chromatographed on 250 g silica gel using ether for elution. The appropriate fractions were evaporated to dryness and the solid recrystallized from isopropylether to yield 11.0 g 4-benzyl-1-(2-methoxyphenyl)-2-piperazinone in the form of yellowish crystals, mp 109°-111°, pure by TLC (ether on silica gel).

Workup

  1. customthe organic phase separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue (27.9 g) in a flask was immersed in a 180°
  6. customoil bath and the formed benzylchloride removed by distillation
  7. customThe crude material was chromatographed on 250 g silica gel
  8. washfor elution
  9. customThe appropriate fractions were evaporated to dryness
  10. customthe solid recrystallized from isopropylether

Sources & evidence

ORD record
ord-796d4c1a83914da2b50736284bef2f2c
Source dataset
uspto-grants-1985_10
Patent number
US04544657

Reaction notes

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