Potassium Carbonate → N,N-dimethyl-4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide

HRID 1601229Notes

Reaction equation

HRID 1601229 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.[CH3:17][N:18]([CH3:34])[C:19](=[O:33])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29]Br)=[C:22]([O:31][CH3:32])[CH:21]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:34][N:18]([CH3:17])[C:19](=[O:33])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][N:12]2[CH2:11][CH2:10][CH:9]([C:6]3[C:5]4[CH:15]=[CH:16][C:2]([F:1])=[CH:3][C:4]=4[O:8][N:7]=3)[CH2:14][CH2:13]2)=[C:22]([O:31][CH3:32])[CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 10358359N,N-dimethyl4 bromopropoxy-3-methoxybenzamide

Product 1

HCID 10049666N,N-dimethyl-4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.9 g, 17.7 mmol), N,N-dimethyl-4-bromopropoxy-3-methoxybenzamide (5.54 g, 17.5 mmol) and K2CO3 (3 g) in acetonitrile (250 ml) was heated at reflux for one hour. At the end of the reaction, the insolubles were filtered and washed with dichloromethane. The solvent was removed on a rotary evaporator. The residue was purified by flash chromatography over a silica gel column. The product thus obtained as an oil weighed 7 g. Crystallization from hot ethanol (45 ml) afforded analytically pure N,N-dimethyl-4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxybenzamide, 3.95 g, 50%, as light yellow crystals, m.p.=126-127° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. customAt the end of the reaction
  4. filtrationthe insolubles were filtered
  5. washwashed with dichloromethane
  6. customThe solvent was removed on a rotary evaporator
  7. customThe residue was purified by flash chromatography over a silica gel column
  8. customThe product thus obtained as an oil
  9. customCrystallization from hot ethanol (45 ml)

Sources & evidence

ORD record
ord-3ceb3d7dbe4f4075b9007c5d1141dceb
Source dataset
uspto-grants-1999_11
Patent number
US05977113

Reaction notes

Loading…