Cyclopropylamine → 4-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester

HRID 2377440Notes

Reaction equation

HRID 2377440 reaction equation
[CH:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13]Br)([CH3:3])[CH3:2].[CH:16]1([NH2:19])[CH2:18][CH2:17]1>C(#N)C>[CH:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][NH:19][CH:16]1[CH2:18][CH2:17]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 574242524-Bromo-2-bromomethyl-benzoic acid isopropyl ester2×

Product 1

HCID 574242534-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl esterYield 28.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred, cooled (ice bath) solution of 4-bromo-2-bromomethyl-benzoic acid isopropyl ester (Intermediate 118, 5.1 g, 15.17 mmol) in acetonitrile (25 mL) was treated with cyclopropyl amine (2 mL, 28.9 mmol). The reaction mixture was allowed to warm to ambient temperature. After 2 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 and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 4-20% ethyl acetate in hexane as the eluent to afforded the title product (1.33 g, 28%).

Workup

  1. customthe volatiles were evaporated in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-ed3eeac71c7b4c83a7ea9b0a968eabf6
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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