Water → HCID 86749897, compound

HRID 864160Notes

Reaction equation

HRID 864160 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.[C:17]([O-])([O-])=[O:18].[K+].[K+].Cl[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1OC)[C:34](=O)[CH2:33][CH2:32][CH2:31]2.C(#N)C.[OH2:44]>>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:24][CH2:25][CH2:26][O:27][CH:28]4[CH2:37][CH2:36][C:35]5[C:30](=[CH:31][C:32]([O:18][CH3:17])=[CH:33][CH:34]=5)[C:29]4=[O:44])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 104457686-(3-Chloropropoxy)-7-methoxy-1-tetralone

Product 1

HCID 86749897HCID 86749897, compound

Procedure

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (0.78 g, 3.6 mmol), K2CO3 (0.60 g, 4.1 mmol), KI (100 mg), 6-(3-chloropropoxy)-7-methoxy-1-tetralone (0.87 g, 3.2 mmol), and acetonitrile (50 ml) was stirred at reflux under nitrogen for 17 hours. The cooled reaction was poured into 100 ml of water and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried with MgSO4 and concentrated to yield 1.7 g of a brown oil. The oil was purified by preparative HPLC (Waters Associates Prep LC/system 500) to afford 1.0 g of a light brown solid. This was combined with an additional sample (2.3 g total) and recrystallization from ethanol yielded 1.7 g. A subsequent recrystallization from ethanol gave 1.25 g (36%) of 6-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-7-methoxy-1-tetralone as a beige powder, m.p.=129°-131 C.

Workup

  1. temperatureat reflux under nitrogen for 17 hours
  2. customThe cooled reaction
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f9ff4d78ba30425f9e4dcb72fea56010
Source dataset
uspto-grants-1996_10
Patent number
US05561128

Reaction notes

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