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

HRID 1284569

Reaction equation

HRID 1284569 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-0e3f17421eeb405881d10764a3a81c41
Source dataset
uspto-grants-1986_01
Patent number
US04563466

Linked notes

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