Potassium Carbonate → HCID 22641500, compound

HRID 2415467Notes

Reaction equation

HRID 2415467 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([OH:17])=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][Cl:30]>CN(C=O)C>[ClH:30].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][O:17][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699943-Methoxybenzyl chlorideHCID 1358041182-Methyl-4-pyrrolidin-1-yl-quinolin-7-ol2×

Product 1

HCID 22641500HCID 22641500, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 114 mg (0.5 mmol) of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol, product of example 2, 166 mg (0.6 mmol) of potassium carbonate and 84 μl (0.6 mmol) of 3-methoxybenzyl chloride was heated at 80° C. in 8 ml of DMF under an argon atmosphere for 23 h. The mixture was cooled to RT and partitioned between EtOAc and water. The organic layer was separated, washed with water then saturated NaCl solution, dried over magnesium sulphate and concentrated in vacuo. The residue was taken up in diethyl ether and some not dissolved material was removed by filtration. The filtrate was treated under stirring with 0.25 ml of 3N HCL in MeOH and stirring was continued for 1 h. The solid that precipitated was filtered off by suction and dried in a high vacuum to give 138 mg (69.7%) of 7-(3-methoxy-benzyloxy)-2-methyl-4-pyrrolidin-1-yl-quinoline hydrochloride as an light-yellow solid. ISP mass spectrum, m/e: 349.4 (M+1 calculated for C22H24N2O2: 349).

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialsaturated NaCl solution, dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. dissolutionsome not dissolved material
  7. customwas removed by filtration
  8. additionThe filtrate was treated
  9. stirringstirring
  10. customThe solid that precipitated
  11. filtrationwas filtered off by suction
  12. customdried in a high vacuum

Sources & evidence

ORD record
ord-44b00df67e3c4cdbab9be36b21152158
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

Loading…