Triethylamine → 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]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]([CH3:20])(O)[CH3:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(N(CC)CC)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(Cl)(Cl)Cl.C(O)C>[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46].[C:30]([O:40][CH2:18][CH:17]([CH3:20])[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][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)[CH2:10][CH2:11]1)(=[O:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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,
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
Sources & evidence
- ORD record
- ord-01d2f340b9284d6581969178b1230709
- Source dataset
- uspto-grants-1996_08
- Patent number
- US05550130
Reaction notes
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