Hydrochloric Acid → HCID 68729707, compound

HRID 2065761Notes

Reaction equation

HRID 2065761 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH:9]1[C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:33]=2[CH3:39])[CH2:28][CH2:27]1)=[O:25])=O)(C)(C)C.Cl>C(O)C>[Cl:23][C:19]1[CH:18]=[C:17]([S:14]([N:11]2[CH2:12][CH2:13][NH:8][CH:9]([C:24]([N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:33]=4[CH3:39])[CH2:28][CH2:27]3)=[O:25])[CH2:10]2)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68726017HCID 68726017, compound

Product 1

HCID 68729707HCID 68729707, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-(3-chloro-benzenesulfonyl)-2-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (2.18 g) in ethanol (21.8 mL) was added a saturated solution of HCl in ethanol (21.8 mL) at 0° C. The reaction mixture was stirred at ambient temperature overnight, the solution was concentrated and the residue dissolved in a mixture of NaHCO3 solution and ethyl acetate. The inorganic phase was extracted with ethyl acetate (×3) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated to yield [4-(3-chloro-benzenesulfonyl)-piperazin-2-yl]-[4-(2,5-dimethyl-phenyl)-piperazin-1-yl]-methanone as crude product (1.79 g), MS: 477.0 ([M+H, 1Cl]+).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionthe residue dissolved in a mixture of NaHCO3 solution and ethyl acetate
  3. extractionThe inorganic phase was extracted with ethyl acetate (×3)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9272e1e21f784f0eb58159f1c58f774f
Source dataset
uspto-grants-2012_10
Patent number
US08288541B2

Reaction notes

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