Sodium Iodide → HCID 46843755, compound

HRID 533771Notes

Reaction equation

HRID 533771 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.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C.O>[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][CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH2:9][C:8]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 66677239HCID 66677239, compound

Product 1

HCID 46843755HCID 46843755, compoundYield 43%

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), 4-(2-chloroethyl)morpholine hydrochloride (99 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). The reaction solution was diluted with H2O, and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated to provide 66 (66 mg, 43% yield) as a yellow solid. LC-MS (M+H=321, obsd.=321).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81aed3b2f669413f9730b976bef3f5b7
Source dataset
uspto-grants-2014_10
Patent number
US08853391B2

Reaction notes

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