Potassium cyanate → N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(1-aminocarbonylpiperidin-4-ylmethyl)amine

HRID 429830Notes

Reaction equation

HRID 429830 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([N:13]([CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:14][CH3:15])[CH3:12])=[CH:6][CH:5]=1.[O-:23][C:24]#[N:25].[K+]>O>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]([N:13]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([C:24]([NH2:25])=[O:23])[CH2:19][CH2:18]2)[CH2:14][CH3:15])[CH3:12])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 18352897N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine hydrochloride

Product 1

HCID 18352825N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(1-aminocarbonylpiperidin-4-ylmethyl)amineYield 77.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine hydrochloride (0.42 grams, 1.16 mmole) and potassium cyanate (1.5 grams, 18.5 mmole) in water (5 ml) was heated under reflux for about 20 minutes. The white solid which formed upon cooling was collected and recrystallized from chloroform/hexane to give N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(1-aminocarbonylpiperidin-4-ylmethyl)amine (0.3 grams, 77%), m.p. 104-10° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for about 20 minutes
  3. customThe white solid which formed
  4. temperatureupon cooling
  5. customwas collected
  6. customrecrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-4b7bf7587c4d4c43a61ba5b87f1779a9
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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