Potassium Carbonate → HCID 15463522, compound

HRID 2379912Notes

Reaction equation

HRID 2379912 reaction equation
[Cl: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:28](=[O:30])[CH3:29])=[CH:24][C:23]=1OC.[C:33]([O-])([O-])=[O:34].[K+].[K+]>C(#N)C>[Cl: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:23]=[CH:24][C:25]([C:28](=[O:30])[CH3:29])=[C:26]([O:34][CH3:33])[CH:27]=4)[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 13076430HCID 13076430, compound

Product 1

HCID 15463522HCID 15463522, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 6-chloro-3-(4-piperidinyl)-1,2-benzisoxazole (4.7 g, 0.02 mol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl] ethanone (4.8 g, 0.02 mol), K2CO3 (2.8 ), several crystals of KI and acetonitrile (120 ml) was refluxed for 16 hours. The reaction was filtered and the filtrate was concentrated to yield a solid-oil mixture. The residue was chromatographed on a Waters Prep 500 utilizing silica columns and eluting with methylene chloride/methanol (5%). Concentration of the desired fractions yielded 3.2 g of a beige solid, which upon recrystallization from ethanol afforded 2.7 (31%) of 1-[4-[3-[4-(6-chloro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone as a beige solid, m.p.=116°-118° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate was concentrated
  4. customto yield a solid-oil mixture
  5. customThe residue was chromatographed on a Waters Prep 500 utilizing silica columns
  6. washeluting with methylene chloride/methanol (5%)

Sources & evidence

ORD record
ord-647fb4417af04f8585457e0c9bc047ca
Source dataset
uspto-grants-1994_11
Patent number
US05364866

Reaction notes

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