Chloroacetyl chloride → HCID 22120221, compound

HRID 1274116Notes

Reaction equation

HRID 1274116 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18].ClCC(Cl)=[O:24].N1CCCC1>C(Cl)Cl.CO.CCOC(C)=O.CCCCCC>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:24])[CH2:15][N:16]2[CH2:19][CH2:20][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 31268PyrrolidineHCID 759941-Benzylpiperazine

Product 1

HCID 22120221HCID 22120221, compoundYield 20%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 1-benzylpiperazine (500 mg, 2.84 mmol) and Et3N (1.2 ml, 8.52 mmol) in CH2Cl2 (15 ml) was dropwise added 2-chloroacetyl chloride via syringe at -78° C. After stirred at -78° C. for 1 h, pyrrolidine (0.24 ml, 2.84 mmol) was then added into the stirred reaction mixture at -78° C. The reaction mixture was then stirred at room temperature for 22 h, then diluted with CH2Cl2 (100 ml), the reaction mixture was washed with aq. Na2CO3 (15 ml), brine, then dried (MgSO4) and concentrated in vacuo. Flash chromatography of the residue (Fuji NH-silica gel 200-300 mesh 20 g, eluent solvents: hexane:AcOEt=1:1, 1:2, 1:5, to CH2Cl2 :MeOH=200:1, 100:1, 10:1) gave a yellow oil (651 mg, 20% yield).

Workup

  1. customat -78° C
  2. stirringThe reaction mixture was then stirred at room temperature for 22 h
  3. washthe reaction mixture was washed with aq. Na2CO3 (15 ml), brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c61f59f851704a0b887474dd359f4505
Source dataset
uspto-grants-2000_12
Patent number
US06156752

Reaction notes

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