Formaldehyde → 2,6-Dimethyl-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 2294826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294826
Cl.[F:2][C:3]1[CH:29]=[CH:28][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]4[C:26]5[CH2:25][CH2:24][NH:23][CH2:22][C:21]=5[S:20][C:19]=4[CH3:27])[CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.C=O.[C:32]([BH3-])#N.[Na+]>C(O)C>[CH3:27][C:19]1[S:20][C:21]2[CH2:22][N:23]([CH3:32])[CH2:24][CH2:25][C:26]=2[C:18]=1[CH2:17][CH2:16][N:13]1[CH2:14][CH2:15][CH:10]([C:7]2[C:6]3[CH:28]=[CH:29][C:3]([F:2])=[CH:4][C:5]=3[O:9][N:8]=2)[CH2:11][CH2:12]1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 214720513-(2-(4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine hydrochloride

Produkt 1

HCID 537781282,6-Dimethyl-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 0.5 g of 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine hydrochloride in ethanol was added 0.3 ml of 37% formaldehyde solution and the mixture was stirred at room temperature for an hour. To the mixture was added 0.2 g of sodium cyanoborohydride, the mixture was stirred for an hour, and then concentrated. To the residue was added water and extracted with chloroform. The extract was washed with water, dried and concentrated in vacuo. The residue was purified by column chromatography and recrystallized from isopropyl ether to give 2,6-dimethyl-3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine 1/2hydrate as white crystals, m.p. 100°-103° C.

Aufarbeitung

  1. stirringthe mixture was stirred for an hour
  2. concentrationconcentrated
  3. additionTo the residue was added water
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. customrecrystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-67c9c72057bd4dbc832bbcb8e6d61351
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691330

Notizen zur Reaktion

Wird geladen…