Sodium Hydroxide → HCID 15480961, compound

HRID 1280442Notes

Reaction equation

HRID 1280442 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5]Cl.[OH-].[Na+].[OH:10][C:11]1[CH2:19][CH2:18][N:17]2[C:13](=[N:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=32)[C:12]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[H-].[Na+]>CN(C=O)C.CCOCC>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][N:14]1[C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[N:17]2[CH2:18][CH2:19][C:11](=[O:10])[C:12]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:13]12

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 135452099HCID 135452099, compound

Product 1

HCID 15480961HCID 15480961, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

2-Dimethylaminoethylchloride hydrochloride is stirred with 10M aqueous NaOH (4 mL) and ether (20 mL) for one hour. The ether layer is decanted and the aqueous layer is washed with ether (10 ml). The combined ether layers are dried over Na2SO4, decanted, and treated with molecular sieves overnight. To a suspension of ethyl 1,2-dihydro-3-hydroxy-pyrido[1,2-a]benzimidazole-4-carboxylate (1.3 g , 5 mmol) in DMF (25 mL) is added in one portion the ethereal solution. The reaction mixture is stirred for 15 min, then a suspension of sodium hydride (0.6 g, 15 mmol, 60% in oil) in DMF (5 mL) is added in one portion. After stirring at ambient temperature for 15 min, the mixture is heated at 110° C. for 2 h. The mixture is cooled, concentrated, and water is added (20 mL). The resulting mixture is extracted 2X with chloroform (100 mL). The combined organic layers are dried and concentrated to afford ethyl 5-(2-dimethylaminoethyl)-3-oxo-1,2,3,5-tetrahydropyrido [1,2-a]benzimidazole-4-carboxylate.

Workup

  1. customThe ether layer is decanted
  2. washthe aqueous layer is washed with ether (10 ml)
  3. dry with materialThe combined ether layers are dried over Na2SO4
  4. customdecanted
  5. additiontreated with molecular sieves overnight
  6. additionis added in one portion the ethereal solution
  7. additionis added in one portion
  8. stirringAfter stirring at ambient temperature for 15 min
  9. temperatureThe mixture is cooled
  10. concentrationconcentrated
  11. additionwater is added (20 mL)
  12. extractionThe resulting mixture is extracted 2X with chloroform (100 mL)
  13. customThe combined organic layers are dried
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-7c44340fd2ee411b9c3e3c772d523884
Source dataset
uspto-grants-2002_09
Patent number
US06451809B2

Reaction notes

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