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

HRID 1869960Notes

Reaction equation

HRID 1869960 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-72dda06c916141a2a04170fa20a9ac9d
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

Loading…