Benzaldehyde → HCID 14536411, compound

HRID 1607876Notes

Reaction equation

HRID 1607876 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14](O)[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[N:17]1([CH:14]2[C:15]3[C:10](=[N:9][C:8]4[C:3]([C:2]=3[NH2:1])=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:11][CH2:12][CH2:13]2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 3655VelnacrineHCID 8083Morpholine

Product 1

HCID 14536411HCID 14536411, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-Amino-1,2,3,4-tetrahydroacridin-1-ol (15.0 g) was refluxed in 1000 ml of toluene that contained 12.18 g of morpholine and 9.285 g of benzaldehyde that had been freshly washed in K2CO3. The reaction mixture wasrefluxed overnight and allowed to cool. It was then filtered off and the crude product was purified by flash chromatography (20% PrOH/EtOAc) to give 2.20 g of analytically pure product after recrystallization from benzene/pentane, m.p. 215°-217°.

Workup

  1. washhad been freshly washed in K2CO3
  2. temperatureto cool
  3. filtrationIt was then filtered off
  4. customthe crude product was purified by flash chromatography (20% PrOH/EtOAc)
  5. customto give 2.20 g of analytically pure product
  6. customafter recrystallization from benzene/pentane, m.p. 215°-217°

Sources & evidence

ORD record
ord-ad3781e7492743b690a8588c1ec76eb6
Source dataset
uspto-grants-1989_09
Patent number
US04868177

Reaction notes

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