Sodium Bicarbonate → HCID 86760176, compound

HRID 1792673Notes

Reaction equation

HRID 1792673 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]([CH:28]([CH3:30])[OH:29])=[CH:24][C:23]=1[OH:31].C([O-])(O)=O.[Na+]>CC#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[CH:27]=[CH:26][C:25]([C:28](=[CH2:30])[OH:29])=[CH:24][C:23]=4[OH:31])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 86760176HCID 86760176, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (4.3 g, 0.0195 mol), 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzenemethanol (4.5 g, 0.0195 mol), KI (200 mg), NaHCO3 (1.8 g, 0.0215 mol) 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 MgSO4, 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]-3-hydroxy-α-methylbenzene 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 MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-6b60c8ddef524a3f8418863c4068ccb3
Source dataset
uspto-grants-2006_07
Patent number
USRE039198E1

Reaction notes

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