Hydrochloric Acid → HCID 46843753, compound

HRID 533770Notes

Reaction equation

HRID 533770 reaction equation
[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][NH:10][CH2:9][C:8]=3[C:4]=2[CH:3]=1.Cl.[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20]Cl)[CH3:17].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].Cl.CCOCC>CN(C=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]3[CH2:12][CH2:11][N:10]([CH2:17][CH2:16][N:18]([CH2:22][CH3:23])[CH2:19][CH3:20])[CH2:9][C:8]=3[C:4]=2[CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 66677239HCID 66677239, compound

Product 1

HCID 46843753HCID 46843753, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (100 mg, 0.48 mmol), 2-diethylaminoethyl chloride hydrochloride (91 mg, 0.53 mmol), K2CO3 (0.08 mL, 1.44 mmol), and NaI (0.02 mL, 0.53 mmol) were suspended in DMF (2 mL), and stirred overnight at room temperature. The reaction solution was diluted with H2O, and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was converted into the HCl salt by dissolving in MeOH and adding 2M HCl in ether (2 equiv.) dropwise. The resulting precipitate was filtered to provide 65 (54 mg, 37% yield) as a white solid. LC-MS (M+H=307, obsd.=307).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionby dissolving in MeOH
  7. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-68bd720d6da74493a1e80f64e164a644
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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