Ammonium Chloride → HCID 66582483, compound

HRID 1972432Notes

Reaction equation

HRID 1972432 reaction equation
[Li][CH2:2]CCC.[F:6][C:7]([F:31])([F:30])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=O.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[S:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[S:22]([N:19]1[CH2:20][CH2:21][N:16]([C:13]2[CH:14]=[CH:15][C:10]([C:8]([C:7]([F:31])([F:30])[F:6])=[CH2:2])=[CH:11][CH:12]=2)[CH2:17][CH2:18]1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 66583043HCID 66583043, compoundHCID 178418339Butyllithium

Product 1

HCID 66582483HCID 66582483, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (0.59 mL, 2.5 M solution in toluene, 1.5 mmol) was added to a stirring mixture of methyltriphenylphosphonium bromide (0.53 g, 1.5 mmol) and THF (3.1 mL) at room temperature under a nitrogen atmosphere. After 30 min, a mixture of 2,2,2-trifluoro-1-(4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)ethanone (0.50 g, 1.2 mmol) and THF (3.1 mL) was added. After an additional 1 h, saturated aqueous ammonium chloride (25 mL) was added, the mixture was partitioned between EtOAc (50 mL) and saturated aqueous ammonium chloride (25 mL). The layers were separated, the organic material was washed sequentially with saturated aqueous ammonium chloride (25 mL) and brine (25 mL), and dried (Na2SO4) purified via column chromatography (10 g of silica, 20% EtOAc in hexanes) to provide 1-(2-thiophenylsulfonyl)-4-(4-(1-(trifluoromethyl)ethenyl)phenyl)piperazine (0.23 g) as an off-white solid.

Workup

  1. additionwas added
  2. waitAfter an additional 1 h
  3. customthe mixture was partitioned between EtOAc (50 mL) and saturated aqueous ammonium chloride (25 mL)
  4. customThe layers were separated
  5. washthe organic material was washed sequentially with saturated aqueous ammonium chloride (25 mL) and brine (25 mL)
  6. dry with materialdried (Na2SO4)
  7. custompurified via column chromatography (10 g of silica, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2eaadfe5846b43d5b667505842d61b14
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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