Nicotinic Acid → N-nicotinoyl dopamine

HRID 1085167

反応式

HRID 1085167 の反応式
Br.[NH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1.[C:13](O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[C:13]([NH:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1

参加物

5

反応物 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 715644-(2-Aminoethyl)pyrocatechol hydrobromide

生成物 1

HCID 13473418N-nicotinoyl dopamine収率 70%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a pyridine solution containing 11.7 g (0.05 mol) dopamine hydrobromide and 6.15 g (0.05 mol) nicotinic acid at 0° C. were added 10.3 g (0.05 mol) dicyclohexylcarbodiimide (DCC). The reaction mixture was stirred at room temperature for 24 hours and the formed dicyclohexylurea was removed by filtration. The pyridine was removed in vacuo and the residue was crystallized from water at 0° C. The product was isolated by filtration and dried over phosphorous pentoxide. Recrystallization from isopropanol gave 9.0 g (0.035 mol), 70% N-nicotinoyldopamine, m.p. 159°-162° C.; aqueous solution of the compound gave a green color with Fe+3 and reduced AgNO3 ; ir (KBr) 3300, 2960, 1725, 1630, 1590, 1520, 1430, 1290, 1190, 1115, 720 and 710 cm-1. NMR (d6 -DMSO) δ 9.25-6.25 (m, 7H), 3.3 (m, 2H) and 2.65 (m, 2H) ppm. Anal. (C14H14N2O 3) C, H, N.

後処理

  1. customthe formed dicyclohexylurea was removed by filtration
  2. customThe pyridine was removed in vacuo
  3. customthe residue was crystallized from water at 0° C
  4. customThe product was isolated by filtration
  5. dry with materialdried over phosphorous pentoxide
  6. customRecrystallization from isopropanol

出典と根拠

ORDレコード
ord-68da145db3c44cb78ce97aa618e32c49
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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