4-Chlorobenzylamine → HCID 178500503, compound

HRID 505219Notes

Reaction equation

HRID 505219 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH3:10][O:11][CH:12]([O:16][CH3:17])[C:13](=O)[CH3:14]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]/[N:7]=[C:13](/[CH3:14])\[CH:12]([O:16][CH3:17])[O:11][CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 178500503HCID 178500503, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three-necked round bottomed flask equipped with a Dean Stark trap and reflux cooler, a solution of 4-chlorobenzylamine (97.3 g, 0.687 mol) and 1,1-dimethoxy-propan-2-one (89.5 g, 0.758 mol) in toluene (300 mL) was heated for 3 h at reflux. The reaction mixture was cooled down and the solvent removed in vacuo to yield the title compound as a pale yellow oil (166 g, 0.687 mol, 100%). MS (ES+): 242 (M(C12H1635ClNO2)+H)+.MS (ES+): 242 (M+H)+.

Workup

  1. customIn a three-necked round bottomed flask equipped with a Dean Stark trap
  2. temperaturereflux cooler
  3. temperatureat reflux
  4. temperatureThe reaction mixture was cooled down
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-43bb621fe1d4438695836ddac7884d36
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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