Chloroform → HCID 15839267, compound

HRID 1735140Notes

Reaction equation

HRID 1735140 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[CH2:20]([O:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25])[CH3:21].C(Cl)(Cl)Cl>O>[CH2:20]([O:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH:25][CH2:2][C:3]([NH:5][C:6]1[C:7]2[C:12]([N:13]=[C:14]3[C:19]=1[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH3:21]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 76507L-Alanine ethyl esterHCID 144713012-Chloro-N-(1,2,3,4-tetrahydroacridin-9-yl)acetamide

Product 1

HCID 15839267HCID 15839267, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5 g of 9-chloroacetylamino-1,2,3,4-tetrahydroacridine, was added 22 g of L-alanine ethyl ester and the reaction was continued for 30 minutes at 100° C. After cooled to room temperature, the reaction mixture was added with 100 ml of chloroform and 100 ml of water and stirred. The chloroform layer was dried over anhydrous sodium sulfate and purified by silica gel column chromatography (chloroform-methanol), followed by recrystallization from chloroform-n-hexane to obtain 5.9 g of the titled compound having the melting point of 101° to 102° C.

Workup

  1. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  2. custompurified by silica gel column chromatography (chloroform-methanol)
  3. customfollowed by recrystallization from chloroform-n-hexane

Sources & evidence

ORD record
ord-e51c44fd67d14dc5b53f5026603e1ee6
Source dataset
uspto-grants-1996_07
Patent number
US05536728

Reaction notes

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