Hydrochloric Acid → HCID 69655664, compound

HRID 11726Notes

Reaction equation

HRID 11726 reaction equation
[O-]CC.[Na+].[Cl:5][C:6]1[CH:31]=[CH:30][C:9]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:8]([C:32]2[O:36][N:35]=[CH:34][CH:33]=2)[CH:7]=1.Cl.O>C(O)C>[Cl:5][C:6]1[CH:31]=[CH:30][C:9]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:8]([C:32](=[O:36])[CH2:33][C:34]#[N:35])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723922Sodium ethoxideHCID 696553762-(4-Chloro-2-isoxazol-5-yl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone

Product 1

HCID 69655664HCID 69655664, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred mixture of sodium ethoxide (0.14 g, 1.0 mmol) in ethanol (2 mL) was added 2-(4-chloro-2-isoxazol-5-yl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.465 g, 1.0 mmol) in ethanol (3 mL). The resulting mixture was stirred at ambient temperature for 3 hours. To the reaction was then added 3M hydrochloric acid (2 mL) and the resulting solution was poured into water (30 mL). This was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel gave the title compound (0.34 g).

Workup

  1. extractionThis was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0d5cee49b2a4e9c90b66e67686ca1e3
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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