Hydrochloric Acid → 3-(2-chloroethyl)-6,7,8,9-tetrahydro-7-methoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride

HRID 429941Notes

Reaction equation

HRID 429941 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:7]2=[N:6][C:5]=1[CH3:17].CC(O)C.Cl.[H][H]>[Pd].CO>[ClH:1].[Cl:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH:12]([O:15][CH3:16])[CH2:13][CH2:14][C:7]2=[N:6][C:5]=1[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 183536383-(2-Chloroethyl)-7-methoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 183536413-(2-chloroethyl)-6,7,8,9-tetrahydro-7-methoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochlorideYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10 parts of 3-(2-chloroethyl)-7-methoxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 40 parts of 2-propanol saturated with hydrogen chloride and 160 parts of methanol was hydrogenated at normal pressure and at room temperature with 2.0 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off over diatomaceous earth and the filtrate was evaporated. The oily residue was taken up in 80 parts of 2-propanol and 2,2′-oxybispropane. After stirring overnight at room temperature, the precipitated product was filtered off, washed with a mixture of 2-propanol and 2,2′-oxybispropane and dried in vacuo at 50° C., yielding 7.5 parts (64.0%) of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-7-methoxy-2-methyl4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride; mp. 170° C. (intermediate 4)

Workup

  1. filtrationthe catalyst was filtered off over diatomaceous earth
  2. customthe filtrate was evaporated
  3. filtrationthe precipitated product was filtered off
  4. washwashed with a mixture of 2-propanol and 2,2′-oxybispropane
  5. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-c0fb85fb03e54151bd04c66ed9a56dcc
Source dataset
uspto-grants-2001_11
Patent number
US06320048B1

Reaction notes

Loading…