Nicotinic Acid → N-nicotinoyl dopamine

HRID 4572

반응식

HRID 4572 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 13473418N-nicotinoyl dopamine수율 70%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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. (C14H14N2O3) C, H, N.

후처리

  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

출처 및 근거

ORD 기록
ord-87a034d6b92e4c48b13cd6d203a3de37
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727079

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