Water → 1-[4-(2-Naphthylsulfonyl)piperazinyl]-2-phenoxyethan-1-one

HRID 516998Notes

Reaction equation

HRID 516998 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].[O:21]([CH2:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C(Cl)Cl>[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:29](=[O:30])[CH2:28][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 69703Phenoxyacetyl chlorideHCID 227218151-(Naphthalene-2-sulfonyl)piperazine hydrochloride2×

Product 1

HCID 11515161-[4-(2-Naphthylsulfonyl)piperazinyl]-2-phenoxyethan-1-oneYield 76.33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a two neck round bottom flask, 1-(naphthalene-2-yl-sulfonyl)piperazine hydrochloride (compound 4, 0.639 moles, 0.200 g) and 2-phenoxyacetylchloride (0.639 moles, 0.109 g) were charged in DCM (20 mL). TEA (2.557 moles, 0.258 g) was added slowly to the reaction flask. The resulting mixture was stirred for 3 h at room temperature. After completion of the reaction, water (10 mL) was added and extracted with DCM (2×20 mL). The combined organic layers were washed with brine (1×20 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel 60-120, 4:6, Ethyl acetate/Hexane) to obtain the title compound (0.200 g, 76.33%).

Workup

  1. additionwas added
  2. extractionextracted with DCM (2×20 mL)
  3. washThe combined organic layers were washed with brine (1×20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (Silica gel 60-120, 4:6, Ethyl acetate/Hexane)

Sources & evidence

ORD record
ord-9ba601d60c124c04a9cc67d75af81fd7
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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