Potassium Carbonate → HCID 59164568, compound

HRID 1441694Notes

Reaction equation

HRID 1441694 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([CH3:19])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][O:30][CH3:31]>C(#N)C>[CH3:31][O:30][CH2:29][CH2:28][CH2:27][NH:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([CH3:19])[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 68406062HCID 68406062, compound

Product 1

HCID 59164568HCID 59164568, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 500 mg 4-(2-Amino-ethyl)-2-methyl-benzonitrile trifluoro acetate and 756 mg potassium carbonate were stirred in 10 ml acetonitrile at 80° C. for fifteen minutes. Then 279 mg 1-bromo-3-methoxypropane, dissolved in 5 ml acetonitrile, were added dropwise at 80° C. The reaction mixture was stirred under micro wave irradiation at 120° C. for one hour. The cooled reaction mixture was filtered through a pad of celite to remove the salt. Then the solvent was removed in vacuo. The residue was purified by RP-HPLC to obtain 268 mg 4-[2-(3-Methoxy-propylamino)-ethyl]-2-methyl-benzonitrile as its trifluoroacetate salt.

Workup

  1. additionwere added dropwise at 80° C
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through a pad of celite
  4. customto remove the salt
  5. customThen the solvent was removed in vacuo
  6. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-2d70d3f2bc2248fc952733b89ce1c089
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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