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

HRID 235457

반응식

HRID 235457 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-[l-(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.

후처리

  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

출처 및 근거

ORD 기록
ord-4296c2d7ec714dbd88fa98258f5c4ed5
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597842

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