Piperidine → HCID 69585563, compound

HRID 1828197Notes

Reaction equation

HRID 1828197 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12](=[O:14])[CH3:13])=[CH:10][C:5]=2[N:4]([CH3:15])[C:3]1=[O:16].[CH3:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.N1CCCCC1>C1(C)C=CC=CC=1>[C:12]([C:11]([C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[C:3](=[O:16])[N:4]([CH3:15])[C:5]=2[CH:10]=1)=[CH:17][C:18]1[CH:19]=[C:20]([CH3:21])[CH:23]=[CH:24][CH:25]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 121053-MethylbenzaldehydeHCID 22063980HCID 22063980, compound

Product 1

HCID 69585563HCID 69585563, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,3-Dimethyl-5-(2-oxo-propyl)-1,3-dihydro-benzoimidazol-2-one was diluted with toluene (30 mL) and treated with 3-methylbenzaldehyde (0.82 mL) and piperidine (0.3 mL). The mixture was placed in an oil bath set to a temperature of 145° C. and the flask was fitted with a pressure equalizing funnel containing 4 Å molecular sieves and equipped with a condenser. After 18 hours the mixture was allowed to cool and was concentrated. Chromatography on silica gel afforded 5-(1-Acetyl-2-m-tolyl-vinyl)-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (1.077 g).

Workup

  1. customThe mixture was placed in an oil bath
  2. customset to a temperature of 145° C. and the flask was fitted with a pressure
  3. additioncontaining 4 Å molecular sieves
  4. customequipped with a condenser
  5. temperatureto cool
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-5bdebf569dc04dbfb56bba9ff35cc27b
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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