L-Methionine → HCID 9864006, compound

HRID 650719Notes

Reaction equation

HRID 650719 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:22]3[C:13](=[N:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:12][CH2:11][C:10]=2[CH2:23][N:24]([CH3:26])[CH3:25])[CH:6]=[CH:7][CH:8]=1.N[C@H](C(O)=O)CCSC>CS(O)(=O)=O>[CH3:26][N:24]([CH2:23][C:10]1[CH2:11][CH2:12][C:13]2[C:22](=[CH:21][C:20]3[C:15]([N:14]=2)=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:9]=1[C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1)[CH3:25]

Participants

4

Reactant 2

HCID 6137L-MethionineHCID 21713197HCID 21713197, compound

Product 1

HCID 9864006HCID 9864006, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
20 °C

Procedure

5.4 g [1-(3-methoxy-phenyl)-3,4-dihydro-acridin-2-yl-methyl]-dimethylamine base were treated at room temperature with 40 ml methanesulfonic acid and 5.4 g methionine. The reaction mixture was stirred for ten days at 20° C. and was evaporated to dryness under vacuum. The solid was dissolved in water, the solution was covered with ethyl acetate, and the mixture was made alkaline with saturated sodium carbonate solution. The aqueous phase was extracted three times with 200 ml portions of ethyl acetate each time, and the combined organic phases were dried over magnesium sulfate and evaporated to dryness under vacuum. 2.4 g [3-(2-dimethylaminomethyl-3,4-dihydro-acridin-1-yl)]-phenol base were obtained. Dissolution of the yellow, amorphous solid in acetone with heating, followed by treating the solution with trimethylchlorosilane and water in equimolar amounts, gave 2.3 g [3-(2-dimethylaminomethyl-3,4-dihydro-acridin-1-yl)]-phenol hydrochloride (48% theoretical) in the form of light yellow crystals. (m.p.: >250° C.).

Workup

  1. customwas evaporated to dryness under vacuum
  2. dissolutionThe solid was dissolved in water
  3. extractionThe aqueous phase was extracted three times with 200 ml portions of ethyl acetate each time
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-71e75fa25a3740e0893372b179600729
Source dataset
uspto-grants-2001_08
Patent number
US06274768B1

Reaction notes

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