Acetonitrile → HCID 15340826, compound

HRID 1459767Notes

Reaction equation

HRID 1459767 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C1(S(O[CH2:27][CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH:37][C:38](=[O:40])[CH3:39])(=O)=O)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].C(#N)C>O>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:27][CH2:28][CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[NH:37][C:38](=[O:40])[CH3:39])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 21960096N-[2-(3-phenylsulfonyloxypropoxy)phenyl]acetamide

Product 1

HCID 15340826HCID 15340826, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.4 g, 16 mmol), N-[2-(3-phenylsulfonyloxypropoxy)phenyl]acetamide (5.3 g, 16 mmol), K2CO3 (2.2 g), and acetonitrile (50 ml) was stirred and refluxed for 5 hours. The reaction was poured into water, and the aqueous suspension was extracted with ethyl acetate. The ethyl acetate was washed (water and brine), dried (MgSO4) and the solvent was concentrated to afford 6.0 g of a thick, brown oil. The oil was chromatographed on a Waters Prep 500 LC on silica gel. Concentration of the appropriate fractions afforded 3.0 g of a beige solid. This was recrystallized from ethyl acetate to yield (with concentration of the mother liquors) 2.2 g (33%) of N-[2-1-[[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]phenyl]acetamide as a beige solid, m.p.=118°-120° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. extractionthe aqueous suspension was extracted with ethyl acetate
  3. washThe ethyl acetate was washed (water and brine)
  4. dry with materialdried (MgSO4)
  5. concentrationthe solvent was concentrated
  6. customto afford 6.0 g of a thick, brown oil
  7. customThe oil was chromatographed on a Waters Prep 500 LC on silica gel

Sources & evidence

ORD record
ord-883a72f588ac4b15a9f10a16b9919820
Source dataset
uspto-grants-1998_12
Patent number
US05854243

Reaction notes

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