Benzaldehyde → HCID 54070128, compound

HRID 1247939Notes

Reaction equation

HRID 1247939 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:15]=1)[C:7](=[O:14])[C:8]1[CH2:13][CH2:12][CH2:11][C:9]=1[N:10]=2.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[O-].[Na+]>CO>[CH:16](=[C:11]1[C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:15][N:6]3[C:7](=[O:14])[C:8]=2[CH2:13][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10942334Sodium MethoxideHCID 124855822,3-Dihydro-7-methylcyclopenta[d]pyrido[1,2-alpha]pyrimidin-10(1H)-one

Product 1

HCID 54070128HCID 54070128, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-methyl-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one (5 g) was reacted with benzaldehyde (13.2 g) in methanol (200 ml) in the presence of sodium methoxide (6.8 g) at reflux temperature for 96 hours. After cooling and concentration in vacuo to a small volume the precipitate was filtered and washed with water until neutral; crystallization from CH2Cl2 /methanol gave 3-benzylidene-7-methyl-1,2,3,10-tetrahydro-cyclopenta[d]pyrido[1,2-a]pyrimidine-10-one, m.p. 197°-199° C., NMR (CDCl3) δ ppm: 2.45 (s) (3H, CH3), 3.10 (bs) (4H, C-1 and C-2 protons), 7.2-7.7 (m) (8H, =CH-- and C-5 and C-6 and phenyl protons), 8.80 (bs) (1H, C-8 proton).

Workup

  1. temperatureat reflux temperature for 96 hours
  2. temperatureAfter cooling
  3. concentrationconcentration in vacuo to a small volume the precipitate
  4. filtrationwas filtered
  5. washwashed with water until neutral
  6. customcrystallization from CH2Cl2 /methanol

Sources & evidence

ORD record
ord-5e467be65e4944dabed7ec924b2ca33a
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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