Water → HCID 21713196, compound

HRID 1421485Notes

Reaction equation

HRID 1421485 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]([CH2:24][N:25]([CH3:27])[CH3:26])[CH2:12][C:13]3[C:22]([CH:23]=2)=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=3)[CH:7]=[CH:8][CH:9]=1.C[Si](C)(C)[Cl:30].O>CC(C)=O>[ClH:30].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:23]3[C:22](=[N:21][C:20]4[C:15]([CH:14]=3)=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:13][CH2:12][C:11]=2[CH2:24][N:25]([CH3:26])[CH3:27])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 9864693HCID 9864693, compound

Product 1

HCID 21713196HCID 21713196, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

18 g of the product from Step 1 were dissolved in 200 ml methanol under dry nitrogen. The reaction mixture was treated with 7.7 g 2-aminobenzaldehyde as the hydrochloride and was subsequently heated to 80° C. After adding 400 ml 1 N hydrochloric acid, the reaction solution was stirred for eight days at 80° C. After cooling to room temperature, the reaction mixture was diluted with 200 ml ethyl acetate and was made alkaline with concentrated sodium hydroxide solution while being cooled in ice. The aqueous phase was extracted three times with 100 ml portions of ethyl acetate each time, and the combined organic phases were dried over magnesium sulfate and evaporated to dryness under vacuum. The residue was eluted and purified by column chromatography on silica gel using ethyl acetate/methanol in a ratio of 4/1. The first product fraction contained 5.4 g [3-(3-methoxy-phenyl)-1,2-dihydro-acridin-2-yl-methyl]-dimethylamine base in the form of beige crystals. In order to prepare the hydrochloride, the solid was dissolved with heating in 200 ml acetone and was treated with trimethylchlorosilane and water in equimolar amounts. 5.2 g (28.3% theoretical) [3-(3-methoxy-phenyl)-1,2-dihydro-acridin-2-yl-methyl]-dimethyl-amine hydrochloride were obtained (light yellow crystals, m.p.: 201° C. to 204° C.). 4.4 g [1-(3-methoxy-phenyl)-3,4-dihydro-acridin-2-yl-methyl]-dimethylamine base in the form of a beige, amorphous solid was obtained as the second fraction. To release the hydrochloride, the solid was dissolved with heating in 200 ml acetone and was treated with trimethylchlorosilane and water in equimolar amounts. 4.2 g (22.90% theoretical) [1-(3-methoxy-phenyl)-3,4-di-hydro-acridin-2-yl-methyl]-dimethylamine hydrochloride were obtained in the form of light yellow crystals, m.p.: 195° C. to 198° C.

Workup

  1. dissolutionthe solid was dissolved

Sources & evidence

ORD record
ord-f776aae3fb3d4bc89b9ce5c9dd590d43
Source dataset
uspto-grants-2000_06
Patent number
US06077845

Reaction notes

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