Hydrochloric Acid → cis-2-[4-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butyl]hexahydro-1H-isoindole-1,3-dione hydrochloride

HRID 266989

Reaktionsgleichung

Reaktionsgleichung von HRID 266989
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=3[O:14][N:13]=2)[CH2:8][CH2:7]1.[C@@H:22]12[C:31](=O)[O:30][C:28](=[O:29])[C@@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27]2.[ClH:33]>N1C=CC=CC=1.C(O)C>[ClH:33].[F:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([CH:9]3[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:1]4[C:28](=[O:29])[C@H:23]5[C@H:22]([CH2:27][CH2:26][CH2:25][CH2:24]5)[C:31]4=[O:30])[CH2:7][CH2:8]3)=[N:13][O:14][C:15]=2[CH:20]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 641660Hexahydrophthalic anhydride, cis-HCID 219600491-(4-Aminobutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine

Produkt 1

HCID 67071030cis-2-[4-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butyl]hexahydro-1H-isoindole-1,3-dione hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

A mixture of 1-(4-aminobutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (4.7 g, 16.1 mmol) and cis-1,2-cyclohexanedicarboxylic anhydride (3.23 g, 21 mmol) in pyridine (45 ml) was heated at reflux for 8 hours. At the end of the reaction, pyridine was removed to dryness. The crude product was purified on a silica gel column. The material thus obtained weighed 3.18 g (45%) as a clear oil. This oil was dissolved in ethanol (15 ml), then was treated with HCl in ethanol (45 ml). Crystallization took place upon cooling. The crystals were collected, 3.2 g, m.p.=229°-231° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. customwas removed to dryness
  4. customThe crude product was purified on a silica gel column
  5. customThe material thus obtained
  6. customCrystallization
  7. temperatureupon cooling
  8. customThe crystals were collected

Quellen und Nachweise

ORD-Eintrag
ord-1a2535dbed574441bd4edceaff38c07e
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652241

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