Sodium Iodide → HCID 86740381, compound

HRID 464650Notes

Reaction equation

HRID 464650 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][CH2:23][CH: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:34](=O)([O-:36])[O-:35].[Na+].[Na+].[I-].[Na+].CC(C)CC(=[O:47])C>>[C:34]([OH:36])(=[O:35])/[CH:9]=[CH:14]/[C:13]([OH:15])=[O:47].[NH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:25]([CH: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][CH2:21]2)=[CH:26]1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 20262428HCID 20262428, compound

Product 1

HCID 86740381HCID 86740381, compoundYield 48%

Procedure

A mixture of 4.5 parts of 7-(3-chloropropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione monohydrochloride, 3 parts of 3-(4-piperidinyl)-1H-indol, 8 parts of sodium carbonate, 0.1 parts of sodium iodide and 240 parts of 4-methyl-2-pentanone was stirred and refluxed for 20 hours. The whole was filtered while hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (92:8 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in 2-propanol. The salt was filtered off and dried, yielding 3.9 parts (48%) of 3,7-dihydro-7-[3-[4-(1H-indol-3-yl)-1-piperidinyl]propyl]-1,3-dimethyl-1H-purine-2,6-dione (E)-2-butenedioate(1:1); mp. 222.7° C. (compound 13).

Workup

  1. temperaturerefluxed for 20 hours
  2. filtrationThe whole was filtered while hot and the filtrate
  3. customwas evaporated
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (92:8 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. filtrationThe salt was filtered off
  9. customdried

Sources & evidence

ORD record
ord-f37962265c5343cd9650417255adadd8
Source dataset
uspto-grants-1985_10
Patent number
US04548939

Reaction notes

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