Toluene → HCID 18186422, compound

HRID 1357490Notes

Reaction equation

HRID 1357490 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=O.[CH3:13][C:14]1([CH3:23])[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16](=O)[CH2:15]1.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:13][C:14]1([CH3:23])[C:15]2[C:4](=[O:6])[C:3]3[C:2](=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:1][C:16]=2[CH2:17][C:18]([CH3:21])([CH3:20])[CH2:19]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 6877Ethyl 2-aminobenzoateHCID 843993,3,5,5-Tetramethylcyclohexanone

Product 1

HCID 18186422HCID 18186422, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.49 ml (10 mmol) of ethyl 2-aminobenzoate and 1.73 ml (10 mmol) of 3,3,5,5-tetramethyl-cyclohexanone were mixed with 20 ml of toluene. 20 mg (0.1 mmol) of para-toluenesulfonic acid was added, and the reaction mixture was refluxed with continuous removal of the water produced in the reaction. After 9 h, toluene was removed under vacuum, and the residue was refluxed in 10 ml of phenyl ether. After cooling, the precipitate was filtered and washed with diethyl ether to obtain 1,1,3,3-tetramethyl-1,2,3,4-tetrahydro-9(10H)-acridone (18%). Following the procedure of Step 3 in Example 1, but substituting 1,1,3,3-tetramethyl-1,2,3,4-tetrahydro-9(10H)acridone for 9-(10H)acridone, gave 9-chloro-1,1,3,3-tetramethyl-1,2,3,4-tetrahydroacridine (21%), which was reacted with 4-(4-methylpiperazin-1-yl)aniline (according to the procedure of Step 4 in Example 1), to afford the title compound (3%, overall yield 0,1%).

Workup

  1. customproduced in the reaction
  2. customtoluene was removed under vacuum
  3. temperaturethe residue was refluxed in 10 ml of phenyl ether
  4. temperatureAfter cooling
  5. filtrationthe precipitate was filtered
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ccd8932b995549c4933336f062a29183
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

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