Water → [[1-(2-Naphthalenylmethyl)-4-piperidinyl]aminocarbonyl]-2-furancarboxamide

HRID 3893Notes

Reaction equation

HRID 3893 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(N)=O)=[O:25].[OH2:30].N1C=CC=C[CH:32]=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:32]([C:21]2[CH:22]=[CH:23][O:19][C:20]=2[C:24]([NH2:26])=[O:25])=[O:30])[CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73100N-(Aminocarbonyl)-2-furancarboxamideHCID 111958234-Amino-1-(2-naphthyl)methylpiperidine

Product 1

HCID 86740590[[1-(2-Naphthalenylmethyl)-4-piperidinyl]aminocarbonyl]-2-furancarboxamide

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, 3/4H2O 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-fab15c502e684fbfa88cc582949b25fa
Source dataset
uspto-grants-1988_02
Patent number
US04722930

Reaction notes

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