Water → HCID 11128828, compound

HRID 1167398Notes

Reaction equation

HRID 1167398 reaction equation
O=[C:2]([CH2:12][CH3:13])[CH2:3][CH:4]1[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]1=[O:11].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1(C)C=CC=CC=1>[CH2:12]([C:2]1[N:21]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:11])[C:4]=2[CH:3]=1)[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 7504BenzylamineHCID 111596842-(2-Oxobutyl)-1,3-cyclohexanedione

Product 1

HCID 11128828HCID 11128828, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2-oxobutyl)cyclohexane-1,3-dione (1000 gms, 4.995 moles) was suspended in toluene (6000 ml, 6 vol). The mixture was warmed to 85 deg C. and stirred for 5minutes. Benzylamine (562.6 gms, 5.25 moles, 1.05 eq) was added dropwise over ˜30-45 minutes. Following the addition the mixture turned to an amber colored solution. Heat was applied to the solution and water was azeotroped off until the reaction temperature reached 110° C. The reaction was allowed to stir at 110° C. for 2 hrs at which time ˜4000 mls of solvent was distilled off at atmospheric pressure. Solution was transferred to a flask and further evaporated to an amber viscous oil which was used directly in the following step.

Workup

  1. temperatureThe mixture was warmed to 85 deg C
  2. additionthe addition the mixture
  3. temperatureHeat
  4. customwas azeotroped off until the reaction temperature
  5. customreached 110° C
  6. stirringto stir at 110° C. for 2 hrs at which time ˜4000 mls of solvent
  7. distillationwas distilled off at atmospheric pressure
  8. customSolution was transferred to a flask
  9. customfurther evaporated to an amber viscous oil which

Sources & evidence

ORD record
ord-ccb4e962cf8743e58f92f573bc898548
Source dataset
uspto-grants-2003_09
Patent number
US06617460B1

Reaction notes

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