Nicotinic Acid → Tryptamide

HRID 1085176

反応式

HRID 1085176 の反応式
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

参加物

5

反応物 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 67652Tryptamine hydrochloride

生成物 1

HCID 65768Tryptamide収率 72.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c0a86adf53aa42fea3cccf41424af423
出典データセット
uspto-grants-1991_04
特許番号
US05008257

関連ノート

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