Potassium Carbonate → 3-bromo-4-chloro-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl-benzamide

HRID 1485936Notes

Reaction equation

HRID 1485936 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1O)[CH3:8])=[O:6].[C:20]([O-:23])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:23][CH2:20][CH2:5][N:7]([CH3:9])[CH3:8])[CH3:8])=[O:6]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 686031173-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide

Product 1

HCID 686036073-bromo-4-chloro-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl-benzamideYield 39.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (404 mg, 1.18 mmol, Step 3B), β-dimethylaminobromide hydrobromide (553 mg, 2.38 mmol) and K2CO3 (655 mg, 4.75 mmol) was heated in DMF (7 mL) at 80° C. for 14 hrs. The mixture was then diluted with ethyl acetate and water. The organic layer was separated and washed with water and brine, dried over Na2SO4, then purified by silica gel column chromatography eluting with DCM/MeOH (95/5 with gradient to 9/1) to yield 3-bromo-4-chloro-N-[2-(2-dimethylamino-ethoxy)-phenyl]-N-methyl-benzamide (97 mg). MS [M+H]+: 412.7; tR=2.24 min. (method 1)

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. custompurified by silica gel column chromatography
  5. washeluting with DCM/MeOH (95/5 with gradient to 9/1)

Sources & evidence

ORD record
ord-7fa0b82661e447f19589492629677f5d
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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