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

HRID 1382445Notes

Reaction equation

HRID 1382445 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-5941afa2a1a5482baf51b1649daf3f71
Source dataset
uspto-grants-1989_02
Patent number
US04806552

Reaction notes

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