Tacrine → HCID 15728805, compound

HRID 2050495Notes

Reaction equation

HRID 2050495 reaction equation
[CH2:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.N1CCOCC1.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[N:15][C:13]2[C:12]3[C:7]([N:6]=[C:5]4[C:14]=2[CH2:1][CH2:2][CH2:3][CH2:4]4)=[CH:8][CH:9]=[CH:10][CH:11]=3)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1935TacrineHCID 8083MorpholineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 15728805HCID 15728805, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (4.0 g) was refluxed in 400 ml of toluene that contained 3.5 g of morpholine and 3.10 g of 4-fluorobenzaldehyde that had been freshly washed in K2CO3. The reaction mixture was refluxed over two (2) nights and then concentrated, purified by flash chromatography (20% EtOAc/CH2Cl2) and recrystallized from dichloromethane/pentane to give 2.20 g of analytically pure product, m.p. 161°-163° C.

Workup

  1. washhad been freshly washed in K2CO3
  2. temperatureThe reaction mixture was refluxed over two (2) nights
  3. concentrationconcentrated
  4. custompurified by flash chromatography (20% EtOAc/CH2Cl2)
  5. customrecrystallized from dichloromethane/pentane
  6. customto give 2.20 g of analytically pure product, m.p. 161°-163° C.

Sources & evidence

ORD record
ord-7b0ee13bec9441c68899b6ff44036f7f
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

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