Benzaldehyde → HCID 23051206, compound

HRID 1651034Notes

Reaction equation

HRID 1651034 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([OH:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.N1CCOCC1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[C:24]1([CH:23]2[NH:1][C:2]3[C:15]4[CH:14]([CH2:13][CH2:12][CH2:11][C:10]=4[N:9]=[C:8]4[C:3]=3[CH:4]=[CH:5][CH:6]=[CH:7]4)[O:16]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 3655VelnacrineHCID 8083Morpholine

Product 1

HCID 23051206HCID 23051206, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-Amino-1,2,3,4-tetrahydroacridine-1-ol (15.0 g) was refluxed in 1 liter of toluene that contained 12.28 g of morpholine and 9.29 g of benzaldehyde that had been freshly washed with K2CO3. The reaction mixture was refluxed overnight and allowed to cool. The crude product was then filtered off and purified by flash chromatography (20% isopropanol/ethyl acetate) to give 8.07 g of a 80:20 mixture of diastereomers after recrystallization from methanol/water. Recrystallization from dimethylformamide/water gave a 60:40 mixture of diastereomers, m.p. 225°-235° C.

Workup

  1. washhad been freshly washed with K2CO3
  2. temperatureThe reaction mixture was refluxed overnight
  3. temperatureto cool
  4. filtrationThe crude product was then filtered off
  5. custompurified by flash chromatography (20% isopropanol/ethyl acetate)
  6. customto give
  7. addition8.07 g of a 80:20 mixture of diastereomers
  8. customafter recrystallization from methanol/water
  9. customRecrystallization from dimethylformamide/water
  10. customgave
  11. additiona 60:40 mixture of diastereomers, m.p. 225°-235° C.

Sources & evidence

ORD record
ord-fd3e9568630247bfbd3def159dc059d0
Source dataset
uspto-grants-1990_05
Patent number
US04927820

Reaction notes

Loading…