Decanoyl chloride → Decanoic acid 1,1-diethyl-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl ester hydrochloride

HRID 2256601Notes

Reaction equation

HRID 2256601 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]([OH:22])([CH2:20][CH3:21])[CH2:18][CH3:19])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:25]([Cl:36])(=[O:35])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].C([O-])(O)=O.[Na+]>C(Cl)Cl>[ClH:36].[CH2:20]([C:17]([O:22][C:25](=[O:35])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([CH2:18][CH3:19])[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:23]=[CH:24][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1)[CH3:21]

Participants

5

Reactant 3

HCID 66982Decanoyl chlorideHCID 516892Sodium BicarbonateHCID 184673426-Fluoro-3-[1-(3-hydroxy-3-ethylpentyl)4-piperidinyl]-1,2-benzisoxazole

Product 1

HCID 86749760Decanoic acid 1,1-diethyl-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl ester hydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-fluoro-3-[1-(3-hydroxy-3-ethylpentyl)-4-piperidinyl]-1,2-benzisoxazole (2.5 g, 7.48 mmol) in DCM (100 ml) was added decanoyl chloride (1.5 ml, 7.48 mmol) at 0 C, under nitrogen. The reaction mixture was stirred for 4 days at which time it was poured into NaHCO3 (sat., 50 ml). The layers were separated and the aqueous phase was extracted with DCM (2X). The combined organics were dried, filtered and concentrated to give the crude product which was purified via flash column chromatography (silica gel, 20-40% EtOAc/DCM). The product containing fractions were concentrated to give 3.0 g (81%) of the desired product as a yellow oil. The hydrochloride salt was prepared in anhydrous ether (60 ml) and isopropanol (1 ml) with ethereal HCl. The white salt was filtered and washed with anhydrous ether, m.p.=159°-161° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with DCM (2X)
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified via flash column chromatography (silica gel, 20-40% EtOAc/DCM)
  8. additionThe product containing fractions
  9. concentrationwere concentrated

Sources & evidence

ORD record
ord-73ed68e246844fc5b2a846fa5931156f
Source dataset
uspto-grants-1997_08
Patent number
US05654319

Reaction notes

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