Water → N-[[[1-(2-Naphthalenylmethyl)-4-piperidinyl]amino]carbonyl]-2-furancarboxamide

HRID 248904노트

반응식

HRID 248904 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)[CH2:4][CH2:3]1.[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24]([NH:26][C:27](N)=[O:28])=[O:25].O>N1C=CC=CC=1>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[CH2:8][N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:27]([NH:26][C:24]([C:20]2[O:19][CH:23]=[CH:22][CH:21]=2)=[O:25])=[O:28])[CH2:7][CH2:6]1

참가 물질

5

반응물 3

HCID 962WaterHCID 73100N-(Aminocarbonyl)-2-furancarboxamideHCID 111958234-Amino-1-(2-naphthyl)methylpiperidine

생성물 1

HCID 19762397N-[[[1-(2-Naphthalenylmethyl)-4-piperidinyl]amino]carbonyl]-2-furancarboxamide수율 17.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

4-Amino-1-(naphth-2-ylmethyl)piperidine (1.2 g, 0.005 m) and 2-furoylurea (0.7 g) in pyridine (5 ml) was refluxed for 6 hours, then cooled. Water was added and the precipitate collected by filtration. The solid was dissolved in chloroform with a little methanol and filtered. The solvent was removed under reduced pressure and the residue was purified by medium pressure liquid chromatography on silica using CHCl3 : MeOH (9:1 v/v) as eluent. The isolated product (1st component eluted) was dissolved in ethyl acetate and acidified with ethanolic HCl to give a precipitate. This was filtered and dried to give 0.3 g of the title compound as the HCl, 3/4 H2O salt, mp. 157°-159° C.

후처리

  1. temperaturecooled
  2. filtrationthe precipitate collected by filtration
  3. dissolutionThe solid was dissolved in chloroform with a little methanol
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by medium pressure liquid chromatography on silica
  7. washThe isolated product (1st component eluted)
  8. dissolutionwas dissolved in ethyl acetate
  9. customto give a precipitate
  10. filtrationThis was filtered
  11. customdried

출처 및 근거

ORD 기록
ord-376c26597ee7462a86d92f44fa69360c
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05212179

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