Sodium Carbonate → HCID 13534172, compound

HRID 464651Notes

Reaction equation

HRID 464651 reaction equation
Cl.Cl[CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:13](=[O:15])[N:12]([CH3:16])[C:11](=[O:17])[N:10]([CH3:18])[C:9]=2[N:8]=[CH:7]1.[NH:19]1[CH2:24][CH:23]=[C:22]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[NH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:25]([C:22]2[CH2:23][CH2:24][N:19]([CH2:3][CH2:4][CH2:5][N:6]3[C:14]4[C:13](=[O:15])[N:12]([CH3:16])[C:11](=[O:17])[N:10]([CH3:18])[C:9]=4[N:8]=[CH:7]3)[CH2:20][CH:21]=2)=[CH:26]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 20262428HCID 20262428, compound

Product 1

HCID 13534172HCID 13534172, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5 parts of 7-(3-chloropropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione monohydrochloride, 4 parts of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole, 8 parts of sodium carbonate and 240 parts of 4-methyl-2-pentanone was stirred for 22 hours at reflux temperature. The whole was stirred till room temperature was reached. The product was filtered off and stirred in water. After filtration, the product was washed with water and stirred in water and an equivalent amount of acetic acid. The mixture was treated with ammonium hydroxide. The precipitated product was filtered off, washed with water and stirred in a mixture of acetonitrile and 2-propanol. The product was filtered off, washed with acetonitrile and dried, yielding 7 parts (98%) of 7-[3-[3,6-dihydro-4-(1H-indol-3-yl)-1(2H)-pyridinyl]propyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione; mp. 243.2° C. (compound 17).

Workup

  1. temperatureat reflux temperature
  2. stirringThe whole was stirred till room temperature
  3. filtrationThe product was filtered off
  4. stirringstirred in water
  5. filtrationAfter filtration
  6. washthe product was washed with water
  7. stirringstirred in water
  8. additionThe mixture was treated with ammonium hydroxide
  9. filtrationThe precipitated product was filtered off
  10. washwashed with water
  11. stirringstirred in a mixture of acetonitrile and 2-propanol
  12. filtrationThe product was filtered off
  13. washwashed with acetonitrile
  14. customdried

Sources & evidence

ORD record
ord-bcf5da0e73a542edaaae5d1f325de01b
Source dataset
uspto-grants-1985_10
Patent number
US04548939

Reaction notes

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