Methyl iodide → 4-Bromo-2-[(cyclopropyl-methylamino)-methyl]-benzoic acid isopropyl ester

HRID 2377441Notes

Reaction equation

HRID 2377441 reaction equation
[CH:1]([O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][NH:14][CH:15]1[CH2:17][CH2:16]1)([CH3:3])[CH3:2].[C:19](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH:1]([O:4][C:5](=[O:18])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][N:14]([CH:15]1[CH2:16][CH2:17]1)[CH3:19])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 574242534-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester2×

Product 1

HCID 574242544-Bromo-2-[(cyclopropyl-methylamino)-methyl]-benzoic acid isopropyl esterYield 88.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester (Intermediate 119, 1.33 g, 4.26 mmol) in acetone (8 mL) was treated with potassium carbonate (2.36 g, 17.05 mmol) and methyl iodide (0.53 mL, 8.52 mmol) and the resulting reaction mixture was stirred at ambient temperature for 3 h. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered over a short bed of silica gel (230-400 mesh) and evaporated in vacuo to afford the title product (1.23 g, 70%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered over a short bed of silica gel (230-400 mesh)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-78c757d018254f6cab808bd42331437d
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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