N-(Aminocarbonyl)-2-thiophenecarboxamide → 1-[1-(Naphth-2-ylmethyl)piperid-4-yl]-3-(then-2-oyl)urea

HRID 248900

Reaction equation

HRID 248900 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.[C:19]([NH:26][C:27](N)=[O:28])([C:21]1[S:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>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:19]([C:21]2[S:25][CH:24]=[CH:23][CH:22]=2)=[O:20])=[O:28])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 395032N-(Aminocarbonyl)-2-thiophenecarboxamideHCID 111958234-Amino-1-(2-naphthyl)methylpiperidine

Product 1

HCID 129423341-[1-(Naphth-2-ylmethyl)piperid-4-yl]-3-(then-2-oyl)urea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Amino-1-(naphth-2-ylmethyl)piperidine (1.0 g, 0.0047 m) and 1-(then-2-oyl)urea (0.65 g, 0.0042 m) in pyridine (5 cm3) was refluxed for 9.5 hours. The solvent was evaporated, water added, and the precipitated title compound filtered and washed well with water. This was recrystallised from ethanol, converted to the hydrochloride salt in ethanol with ethanolic HCl, and recrystallised from ethanol, 0.5 g, at the hydrochloride, m.p. 217°-219° C.

Workup

  1. customThe solvent was evaporated
  2. additionwater added
  3. customthe precipitated title compound
  4. filtrationfiltered
  5. washwashed well with water
  6. customThis was recrystallised from ethanol
  7. customrecrystallised from ethanol, 0.5 g, at the hydrochloride, m.p. 217°-219° C.

Sources & evidence

ORD record
ord-8da90762ae194035855781ccc1a1c76e
Source dataset
uspto-grants-1993_05
Patent number
US05212179

Linked notes

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