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

HRID 248904Notes

Reaction equation

HRID 248904 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-376c26597ee7462a86d92f44fa69360c
Source dataset
uspto-grants-1993_05
Patent number
US05212179

Reaction notes

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