Potassium Carbonate → HCID 89657341, compound

HRID 1775227Notes

Reaction equation

HRID 1775227 reaction equation
[O:1]=[C:2]1[C:14]2[C:13]3[C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5][NH:4][CH2:3]1.Cl.Cl[CH2:21][CH2:22][N:23]([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][N:4]1[CH2:3][C:2](=[O:1])[C:14]2[C:13]3[C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 89657350HCID 89657350, compound

Product 1

HCID 89657341HCID 89657341, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-oxo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-5-carboxylate (183 mg, 0.75 mol) was dissolved in DMF (20 ml) and 2-chloro-N,N-dimethylethanamine hydrochloride (107 mg, 0.75 mmol), and K2CO3 (207 mg, 1.5 mmol) were subsequently added. The reaction was stirred at 50° C. until the starting material was disappeared. The reaction mixture was then diluted with CH2Cl2 (15 ml) and washed with water three times. The organic layer was dried with MgSO4. Evaporation of most of the solvent and the crude product was purified by chromatography column on silica gel (elution with CH2Cl2/MeOH/NH3.H2O) to provide 0.09 g of methyl 2-(2-(dimethylamino)ethyl)-4-oxo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-5-carboxylate. MS (ESI) m/e [M+1]+ 316.

Workup

  1. washwashed with water three times
  2. dry with materialThe organic layer was dried with MgSO4
  3. customEvaporation of most of the solvent
  4. customthe crude product was purified by chromatography column on silica gel (elution with CH2Cl2/MeOH/NH3.H2O)

Sources & evidence

ORD record
ord-9800b76f2f1f4c84a4392c747e928a4a
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

Loading…