Nicotinic Acid → Tryptamide

HRID 1085176

Reaktionsgleichung

Reaktionsgleichung von HRID 1085176
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH2:4][CH2:3][NH:2][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=2)=[CH:6]1

Komponenten

5

Edukt 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 67652Tryptamine hydrochloride

Produkt 1

HCID 65768TryptamideAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 1.97 g (10 mmol) of tryptamine hydrochloride and 1.23 g (10 mmol) of nicotinic acid in 10 ml of dry pyridine at 0° C. were added 2.20 g (10.7 mmol) of dicyclohexylcarbodiimide. The reaction mixture was stirred at room temperature for 24 hrs, and the formed dicyclohexylurea was removed by filtration (2.34 g). The pyridine was removed in vacuo, and 10 ml of methanol were added to the residue. Insoluble dicyclohexylurea in methanol was removed by filtration (0.05 g). The methanol was removed in vacuo and 10 ml of methylene chloride was added to the residue. Insoluble compound in methylene chloride was removed by filtration (0.04 g). The methylene chloride was removed in vacuo and the residue was crystallized from isopropanol. Recrystallization from methanol/isopropanol gave 1.92 g (72.5%) of N-[2-(3-indolyl)ethyl]nicotinamide as pale brown plates, m.p. 150°-152° C. IR (KBr) 3280, 3050, 2940, 1646, 1526, 1412, 1302, 1102, 740, 697 cm-1. Anal. calc. for C16H15N3O: C, 72.42; H, 5.91; N, 15.84. Found: C, 72.51; H, 5.74; N, 15.77.

Aufarbeitung

  1. customthe formed dicyclohexylurea was removed by filtration (2.34 g)
  2. customThe pyridine was removed in vacuo, and 10 ml of methanol
  3. additionwere added to the residue
  4. customInsoluble dicyclohexylurea in methanol was removed by filtration (0.05 g)
  5. customThe methanol was removed in vacuo and 10 ml of methylene chloride
  6. additionwas added to the residue
  7. customInsoluble compound in methylene chloride was removed by filtration (0.04 g)
  8. customThe methylene chloride was removed in vacuo
  9. customthe residue was crystallized from isopropanol
  10. customRecrystallization from methanol/isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-c0a86adf53aa42fea3cccf41424af423
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008257

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