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

HRID 233906

반응식

HRID 233906 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 (2×). 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.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with DCM (2×)
  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

출처 및 근거

ORD 기록
ord-2248463d413b49e0b9ae51dc80b43189
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593995

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