Tetrahydrofuran → 1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine

HRID 2120712

Reaktionsgleichung

Reaktionsgleichung von HRID 2120712
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[N:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1>CCCCCC>[CH2:1]([N:8]1[C:9]2=[N:13][C:14]3[C:15]([C:16]([NH2:17])=[C:10]2[CH2:11][CH2:12]1)=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 8028TetrahydrofuranHCID 7584062-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile

Produkt 1

HCID 7119891-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamineAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

The compound 1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine (Compound 25) was synthesized by first cooling a solution of Compound 24 (37.6 g, 0.14 mol) and tetrahydrofuran (350 mL) to −35° C. under argon atmosphere and adding a solution of hexane (110 mL) and lithium diisopropylamine-tetrahydrofuran complex (0.35 mol) dropwise. The temperature of the mixture was then gradually raised to −10° C. and ice-water (30 mL) was added dropwise. Organic solvent was evaporated under reduced pressure and the mixture was extracted with chloroform. The combined organic extracts were dried with anhydrous sodium sulfate and condensed under vacuum. The residue was treated with ethanol (15 mL) and crystals precipitated. The precipitate was filtered, washed with cold ethanol and dried under vacuum to yield 14.6 g (39%) of Compound 25 as needles; mp 174-176° C.; IR (KBr): 3411, 3116, 1654, 1502, 1350, 756 cm−1; 1H NMR (DMSO-d6): δ 7.01-7.93 (m, 9H), 6.05 (s, 2H), 4.60 (s, 2H), 3.37 (t, 2H), 2.87 (t, 2H); 13C NMR (CDCl3): δ 162.7, 149.3, 144.8, 138.8, 128.7, 128.2, 128.1, 127.2, 126.2, 121.8, 119.9, 117.6, 100.7, 48.4, 23.3. Anal. Calcd. for C18H17N3(275.35): C, 78.52; H, 6.22; N, 15.26. Found: C, 78.07; H, 6.07; N, 15.08.

Aufarbeitung

  1. customThe compound 1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine (Compound 25) was synthesized
  2. customOrganic solvent was evaporated under reduced pressure
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe combined organic extracts were dried with anhydrous sodium sulfate and condensed under vacuum
  5. additionThe residue was treated with ethanol (15 mL) and crystals
  6. customprecipitated
  7. filtrationThe precipitate was filtered
  8. washwashed with cold ethanol
  9. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f4f00e717c714057833e614ae89933b2
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693112B2

Verknüpfte Notizen

Wird geladen…