Hydroxylamine → HCID 21919406, compound

HRID 1244447Notes

Reaction equation

HRID 1244447 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14](/[CH:17]=[CH:18]/[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:28][OH:29]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH:18]([NH:28][OH:29])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([Cl:27])[CH:26]=3)(=[O:15])=[O:16])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 21919378HCID 21919378, compound

Product 1

HCID 21919406HCID 21919406, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-chlorophenyl)-4-{[(1E)-4-(5-chloropyridin-3-yl)but-1-enyl]sulfonyl}piperazine (crude from previous step), in THF (10 mL) at RT was added a solution of hydroxylamine (2 mL, 50% aqueous solution in water). The reaction was stirred for 3 hours at RT before being quenched with saturated aqueous ammonium chloride solution (5 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (3×10 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo. The residue was then purified by flash chromatography (silica, 100% ethyl acetate) to give the title compound (100 mg, 0.22 mmol).

Workup

  1. custombefore being quenched with saturated aqueous ammonium chloride solution (5 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic extracts were then dried, (MgSO4),
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by flash chromatography (silica, 100% ethyl acetate)

Sources & evidence

ORD record
ord-e6564403ef474390ad2a116a5ba7c277
Source dataset
uspto-grants-2006_10
Patent number
US07122551B2

Reaction notes

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