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

HRID 703856ノート

反応式

HRID 703856 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24057015edb24ffa808c77061f2d1bfd
出典データセット
uspto-grants-1991_01
特許番号
US04985438

反応ノート

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