1,2-Dichloroethane → 2-Chloro-1-(4-(3-chlorophenyl)piperazin-1-yl)ethan-1-one

HRID 1094721Notes

Reaction equation

HRID 1094721 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.C(Cl)CCl.[Cl:26][CH2:27][C:28](O)=[O:29]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:26][CH2:27][C:28]([N:12]1[CH2:13][CH2:14][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Cl:2])[CH:4]=2)[CH2:10][CH2:11]1)=[O:29]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 300Chloroacetic AcidHCID 8471TriethylamineHCID 256811-(3-Chlorophenyl)piperazine monohydrochloride

Product 1

HCID 41653802-Chloro-1-(4-(3-chlorophenyl)piperazin-1-yl)ethan-1-oneYield 70.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To solution of 1-(3-chlorophenyl)piperazine hydrochloride (1.2 g, 5.2 mmol) in DCM (10 mL) was added triethylamine (1.0 mL, 7.3 mmol), EDC (1.9 g, 10 mmol), DMAP (cat.) and chloroacetic acid (0.4 g, 5.2 mmol). The reaction was stirred at RT overnight and DCM was removed. The resultant residue was partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was dried over Na2SO4 and concentrated to provide 1.0 g of pure 2-chloro-1-(4-(3-chlorophenyl)piperazin-1-yl)ethanone, (yield: 70%).

Workup

  1. customDCM was removed
  2. customThe resultant residue was partitioned between EtOAc (50 mL) and H2O (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5236cf788a6a4438a99a34d8d9d28dab
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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