Water → N,N,N′-Trimethyl-N′-[1-(phenylmethyl)-4-piperidinyl]urea

HRID 1577838Notes

Reaction equation

HRID 1577838 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].Cl.Cl.[CH2:9]([N:16]1[CH2:21][CH2:20]C(NC)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:24]([N:26](CC)[CH2:27]C)C.O>C(Cl)(Cl)Cl>[CH2:9]([N:16]1[CH2:21][CH2:20][CH:1]([N:2]([CH3:6])[C:3]([N:26]([CH3:27])[CH3:24])=[O:4])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 193693851-Benzyl-N-methylpiperidin-4-amine--hydrogen chloride (1/2)

Product 1

HCID 20569897N,N,N′-Trimethyl-N′-[1-(phenylmethyl)-4-piperidinyl]ureaYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dimethylcarbamoyl chloride (2.7 g) was added slowly to a stirred, cooled solution of 1-benzyl-4-(methylamino)piperidine dihydrochloride (7 g) in dry chloroform (50 ml) and triethylamine (7.7 g). The mixture was then stirred at room temperature for 3 hours and heated under reflux for a further 7 hours. The cooled mixture was treated with water (50 ml), separated, and the chloroform layer dried (MgSO4) and evaporated in vacuo to give 1-(1-Benzylpiperid-4yl)-1,3,3-trimethyl urea (6.5 g) as a mobile oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for a further 7 hours
  3. customseparated
  4. dry with materialthe chloroform layer dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e3eec7cc3a82460aba302d91902bc8f4
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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