Acetonitrile → HCID 19967057, compound

HRID 363583Notes

Reaction equation

HRID 363583 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.Cl[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25](C(C)O)=[CH:24][C:23]=1[OH:31].[C:32]([O-:35])(O)=O.[Na+].[CH3:37]C#N>>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:18][CH2:19][CH2:20][O:21][C:22]4[C:23]([OH:31])=[CH:24][CH:25]=[CH:26][C:27]=4[CH:32]([CH3:37])[OH:35])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 103989864-(3-Chloropropoxy)-3-hydroxy-alpha-methylbenzenemethanol

Product 1

HCID 19967057HCID 19967057, compound

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (4.3 g, 19.5 mmol), 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzenemethanol (4.5 g, 19.5 mmol), KI (200 mg), NaHCO3 (1.8 g, 21.5 mmol) and CH3CN (125 ml) was stirred at reflux under nitrogen for 24 hours. The cooled reaction was filtered and the filter cake was washed with CH3CN. The filtrate was concentrated to afford an oily residue, which was partitioned between water and ethyl acetate. The ethyl acetate extract was washed with water, dried with MgSO, and concentrated to yield 8.6 g of a dark oil. The oil was purified by preparative HPLC (Waters Associates prep LC/system 500) to yield 5.0 g. The compound was recrystallized twice from ethanol to provide 3.9 g (49%) of 4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-propoxy]-3hydroxy-α-methyl-benzene methanol as a light beige solid, m.p.=142°-144° C.

Workup

  1. temperatureat reflux under nitrogen for 24 hours
  2. customThe cooled reaction
  3. filtrationwas filtered
  4. washthe filter cake was washed with CH3CN
  5. concentrationThe filtrate was concentrated
  6. customto afford an oily residue, which
  7. customwas partitioned between water and ethyl acetate
  8. extractionThe ethyl acetate extract
  9. washwas washed with water
  10. dry with materialdried with MgSO
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9b5d9b19c52344d59ceec66cbfa7c18a
Source dataset
uspto-grants-1999_02
Patent number
US05874435

Reaction notes

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