Phenyl isocyanate → 4-[N-methyl-N-(2-phenylethyl)amino]-1-anilinocarbonylpiperidine

HRID 962780Notes

Reaction equation

HRID 962780 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][N:11]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)(Cl)Cl>[CH3:10][N:11]([CH:20]1[CH2:21][CH2:22][N:23]([C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:9])[CH2:24][CH2:25]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 10856966Methyl-phenethyl-piperidin-4-YL-amine

Product 1

HCID 232850024-[N-methyl-N-(2-phenylethyl)amino]-1-anilinocarbonylpiperidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.0 ml of phenyl isocyanate was added to a solution of 1.0 g of 4-[N-methyl-N-(2-phenylethyl)amino]piperidine in 15 ml of chloroform. The mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added diethyl ether for crystallization. The resulting crystals were collected by filtration and recrystallized from ethyl acetate to obtain 0.7 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-anilinocarbonylpiperidine as colorless prism-like crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added diethyl ether
  3. customfor crystallization
  4. filtrationThe resulting crystals were collected by filtration
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-30ff3204a0b64769914115a267d09c51
Source dataset
uspto-grants-1998_06
Patent number
US05760058

Reaction notes

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