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Acetyl chloride → 2-[4-(6-Fluoro-1,2-benzisoxazol-yl)-piperidinyl]ethyl acetamide fumarate

HRID 363626
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 363626
[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16]N)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH2:20]([N:22](CC)CC)[CH3:21].C(Cl)(=[O:29])C.[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35]>C(Cl)Cl.C(O)C>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[F:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:21][C:20]([NH2:22])=[O:29])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1
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Komponenten

7

Edukt 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 444972Fumaric AcidHCID 146998572-(4-(6-Fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethan-1-amine

Produkt 1

HCID 867482572-[4-(6-Fluoro-1,2-benzisoxazol-yl)-piperidinyl]ethyl acetamide fumarate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.56 g, 9.7 mmol) and triethylamine (1.45 g, 14.5 mmol) in DCM (50 ml) was treated with dropwise addition of acetyl chloride (1.0 g, 12.7 mmol) at room temperature. The mixture was stirred for 4 hours at room temperature. The reaction mixture was diluted with DCM and washed with brine. The organic solution was dried over MgSO4 and concentrated to a crude oil. The crude oil was purified by flash chromatography over a silica gel column (SiO2, 20 g; eluted with (0-2%) CH3OH in DCM). The pure product thus obtained weighed 1.36 g (46%). It was converted to a fumarate salt by treatment with fumaric acid (517 mg) in ethanol. Recrystallization from ethanol gave white crystals; weight: 1.53 g, m.p.=132°-133° C.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated to a crude oil
  4. customThe crude oil was purified by flash chromatography over a silica gel column (SiO2, 20 g; eluted with (0-2%) CH3OH in DCM)
  5. customThe pure product thus obtained
  6. customRecrystallization from ethanol
  7. customgave white crystals

Quellen und Nachweise

ORD-Eintrag
ord-18ab4ad5b6534208ba8f3c27c7592053
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05874435

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