Sodium Iodide → 7-chloro-3-(3,5-dimethylphenyl)-4-(1-methyl-piperidin-3-ylmethoxy)-1H-quinolin-2-one

HRID 1857628Notes

Reaction equation

HRID 1857628 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.Cl.Cl[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][N:27]([CH3:31])[CH2:26]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][N:27]([CH3:31])[CH2:26]3)=[C:7]([C:13]3[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2×HCID 1066903-Chloromethyl-1-methylpiperidinium chloride2×HCID 547315327-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one

Product 1

HCID 443224027-chloro-3-(3,5-dimethylphenyl)-4-(1-methyl-piperidin-3-ylmethoxy)-1H-quinolin-2-oneYield 38.7%

Conditions

Temperature
80 °C

Procedure

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-1H-quinolin-2-one (100 mg in 3 mL dry N,N-dimethylformamide) was added 68 mg 3-chloromethyl-1-methylpiperidine hydrochloride followed by 55 mg sodium iodide and 97 mg potassium carbonate and the mixture heated to 80° C. on an oil bath. After 7 hours, an additional portion of potassium carbonate (48 mg) and 3-chloromethyl-1-methylpiperidine hydrochloride (68 mg) were added and the reaction allowed to proceed at 80° C. for another 14 hours. At this time the reaction was cooled to room temperature and quenched by pouring into 25 mL of ice/water. The precipitate was collected by filtration and washed with cold water. Purification of the crude by flash chromatography on silica gel (chloroform: 10% ammonium hydroxide in methanol, 95:5) provided the title compound (53 mg). MASS=411 (M+H)

Workup

  1. waitto proceed at 80° C. for another 14 hours
  2. temperatureAt this time the reaction was cooled to room temperature
  3. customquenched
  4. additionby pouring into 25 mL of ice/water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with cold water
  7. customPurification of the crude by flash chromatography on silica gel (chloroform: 10% ammonium hydroxide in methanol, 95:5)

Sources & evidence

ORD record
ord-96810785dd054f4cb432b5146e8adaff
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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