Diisopropylamine → 6-[2-[4-(1H-indol-1-yl)-1-piperidinyl]ethyl]-1,2,7-trimethylimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 580905Notes

Reaction equation

HRID 580905 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[C:12]([CH3:15])[N:13]([CH3:14])[C:7]2=[N:6][C:5]=1[CH3:16].[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)[CH2:19][CH2:18]1.CC(NC(C)C)C>C(O)C>[N:23]1([CH:20]2[CH2:21][CH2:22][N:17]([CH2:2][CH2:3][C:4]3[C:9](=[O:10])[N:8]4[CH:11]=[C:12]([CH3:15])[N:13]([CH3:14])[C:7]4=[N:6][C:5]=3[CH3:16])[CH2:18][CH2:19]2)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 140907551-(Piperidin-4-yl)-1H-indoleHCID 541674696-(2-bromoethyl)-1,2,7-trimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 700046756-[2-[4-(1H-indol-1-yl)-1-piperidinyl]ethyl]-1,2,7-trimethylimidazo[1,2-a]pyrimidin-5(1H)-oneYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(2-bromoethyl)-1,2,7-trimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one (8.85 g), prepared as described in EP-0,378,255, 1-(4-piperidinyl)-1H-indole (2 g) and N-(1-methylethyl)-2-propanamine (1.2 g) in ethanol (100 ml) was stirred and refluxed for 6 hours. The solvent was evaporated and the residue was stirred in water and subsequently extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN/DIPE and the precipitate was filtered off and dried, yielding 2.5 g (62%) 6-[2-[4-(1H-indol-1-yl)-1-piperidinyl]ethyl]-1,2,7-trimethylimidazo[1,2-a]pyrimidin-5(1H)-one (compound 9; mp. 165.7° C.).

Workup

  1. customprepared
  2. temperaturerefluxed for 6 hours
  3. customThe solvent was evaporated
  4. extractionsubsequently extracted with CH2Cl2
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from CH3CN/DIPE
  12. filtrationthe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-f39c2ad9bd1a468a9343e5bebef65a23
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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