Acridine, 1,2,3,4-tetrahydro-9-chloro- → HCID 18186430, compound

HRID 1357485Notes

Reaction equation

HRID 1357485 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[C:21]1[C:22]2[C:27]([N:28]=[C:29]3[C:34]=1[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:26][CH:25]=[CH:24][CH:23]=2>>[C:17]([O:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][C:6]=2[C:21]2[C:22]3[C:27]([N:28]=[C:29]4[C:34]=2[CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9][CH2:10]1)(=[O:19])[CH3:18]

Participants

3

Reactant 2

HCID 21495Acridine, 1,2,3,4-tetrahydro-9-chloro-HCID 131723971HCID 131723971, compound

Product 1

HCID 18186430HCID 18186430, compoundYield 47%

Procedure

0.14 ml (2.0 mmol) of 2-bromoethanol and 0.17 ml (2.4 mmol) of acetyl chloride were dissolved in 2 ml of dichloromethane. 0.28 ml (2.0 mmol) of triethylamine was added, and the reaction mixture was stirred at room temperature. After 1 h 50 ml of dichloromethane was added to the reaction mixture, which was then washed with a sodium bicarbonate (sat.) solution, a 10% citric acid solution and water. The organic phase was dried over sodium sulfate and evaporated to obtain 0.241 g (72%) of 2-bromoethylacetate. Following the procedure outlined in Step 1 of Example 1, but substituting 2-bromoethylacetate for methyl iodide, afforded 2-[4-(4-nitrophenyl)piperazin-1-yl]ethylacetate (64%), which was reduced according to the procedure of Step 2 in Example 1 to give the corresponding amine 2-[4-(4-aminophenyl)piperazin-1-yl]ethylacetate in quantitative yield. 2-[4-(4-aminophenyl)piperazin-1-yl]ethylacetate was reacted with 9-chloro-1,2,3,4-tetrahydroacridine (according to the procedure of Step 4 in Example 1) to obtain 2-{4-[4-amino-(1,2,3,4-tetrahydroacridin-9-yl)phenyl]piperazin-1-yl}ethyl acetate with 47% yield. Treating the ester with 4 equivalents of lithium hydroxide in a dioxane/water solution overnight, afforded the title compound with 60% yield (overall yield 20%).

Sources & evidence

ORD record
ord-e19d28a0b52442b8b7556908fc551276
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

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