Ethanol → 4-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]2-methylbutyl decanoate fumarate
Reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]([CH2:9][CH2:10][C:11](C)(O)CN3CCCCC3)=[N:7][O:8][C:4]=2[CH:3]=1.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.[C:30](Cl)(=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46].C([OH:52])C>C(Cl)(Cl)Cl>[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46].[C:30]([O:40][CH2:42][CH:43]([CH3:44])[CH2:29][CH2:28][N:25]1[CH2:11][CH2:10][CH:9]([C:6]2[C:5]3[CH:21]=[CH:22][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:27][CH2:26]1)(=[O:52])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]Participants
7
Procedure
To a mixture of 4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl-2-methyl-2-butanol (4.68 g, 15.3 mmol) and triethylamine (2.23 g, 22.3 mmol) in chloroform (20 ml) was added decanoyl chloride (3.5 g, 18.4 mmol, 1.2 eq) dropwise at 0° C. The reaction was stirred at ambient temperature for 4 hours. The solvent was removed. The residue was purified by flash chromatography over a silica gel column (SiO2, 65 g, eluted with DCM, 1 l, 1% CH3OH in DCM, 1 l ). The product thus purified weighed 5.7 g (80%) as an oil. This oily product was converted to the fumarate salt in ethanol with fumaric acid (1.51 g, 1.0 eq) to yield 3.34 g, m.p.=133-134° C.
Workup
- customThe solvent was removed
- customThe residue was purified by flash chromatography over a silica gel column (SiO2, 65 g, eluted with DCM, 1 l, 1% CH3OH in DCM, 1 l )
- customThe product thus purified
- customto yield 3.34 g, m.p.=133-134° C.
Sources & evidence
- ORD record
- ord-6c84abf5a4634160a1f8d0e560e51828
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06043240
Reaction notes
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