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

HRID 3890

Reaction equation

HRID 3890 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-b9261355c50f45a3ac126c2d60770352
Source dataset
uspto-grants-1988_02
Patent number
US04722930

Linked notes

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