Nicotinic Acid → Tryptamide

HRID 1085176

반응식

HRID 1085176 반응식
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

참가 물질

5

반응물 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 67652Tryptamine hydrochloride

생성물 1

HCID 65768Tryptamide수율 72.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0a86adf53aa42fea3cccf41424af423
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05008257

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