Decanoyl chloride → 3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl decanoate fumarate

HRID 267006

Reaktionsgleichung

Reaktionsgleichung von HRID 267006
[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:21](Cl)(=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>C(Cl)Cl.C(O)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[C:21]([O:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:19]=[CH:20][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1)(=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Komponenten

6

Edukt 3

HCID 66982Decanoyl chlorideHCID 444972Fumaric AcidHCID 153849663-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)propan-1-ol

Produkt 1

HCID 219600393-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl decanoate fumarate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propanol (1.81 g, 6.5 mmol) triethylamine (0.9 g, 9.0 mmol) in DCM (45 ml) was added decanoyl chloride (1.5 g, 7.8 mmol) dropwise at room temperature. The mixture was stirred for 20 minutes, then concentrated down to a crude solid. The solid was extracted into EtOAc (20 ml), and the insoluble salts were filtered. The EtOAc was removed. The crude oil was purified by flash choursomatography (Sorbsil C-30, 30 g; eluted with MeOH:DCM). The oil thus obtained (2.54 g, 90%) was converted to a fumarate salt with fumaric acid (670 mg) in ethanol. The crystals collected weighed 1.61 g, m.p.=100°-102° C.

Aufarbeitung

  1. concentrationconcentrated down to a crude solid
  2. extractionThe solid was extracted into EtOAc (20 ml)
  3. filtrationthe insoluble salts were filtered
  4. customThe EtOAc was removed
  5. customThe crude oil was purified by flash choursomatography (Sorbsil C-30, 30 g; eluted with MeOH:DCM)
  6. customThe oil thus obtained (2.54 g, 90%)
  7. customThe crystals collected

Quellen und Nachweise

ORD-Eintrag
ord-72e0295f754940339bc67bbc85f4d5fe
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652241

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