Tacrine → HCID 15728813, compound

HRID 2050501Notes

Reaction equation

HRID 2050501 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.[C:22]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)#[N:23]>C1(C)C=CC=CC=1>[C:22]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[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:26][CH:25]=1)#[N:23]

Participants

5

Reactant 3

HCID 1935TacrineHCID 8083MorpholineHCID 660424-Cyanobenzaldehyde

Product 1

HCID 15728813HCID 15728813, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,2,3,4-Tetrahydro-9-acridinamine (3.2 g) was refluxed in 300 ml of toluene containing morpholine (2.8 g) and 4-cyanobenzaldehyde (2.60 g). After twenty-four (24) hours the reaction mixture was concentrated and purified by flash chromatography. Fractions containing the product were concentrated and recrytallized from CH2Cl2 /pentane to give 2.30 g of product, m.p. 204°-205° C.

Workup

  1. concentrationAfter twenty-four (24) hours the reaction mixture was concentrated
  2. custompurified by flash chromatography
  3. additionFractions containing the product
  4. concentrationwere concentrated

Sources & evidence

ORD record
ord-c6909b4d85584654a562f4dd1d9fbe1d
Source dataset
uspto-grants-1991_05
Patent number
US05013741

Reaction notes

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