Diethylamine → 4-((Diethylamino)methyl)benzoic acid hydrochloride

HRID 2257046Notes

Reaction equation

HRID 2257046 reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13]>C(O)C.[OH-].[Na+]>[ClH:1].[CH2:12]([N:14]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[CH2:15][CH3:16])[CH3:13]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 742344-(Chloromethyl)benzoic acid

Product 1

HCID 122990074-((Diethylamino)methyl)benzoic acid hydrochlorideYield 55.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-chloromethylbenzoic acid (17.1 g, 0.1 mol) in ethanol (200 ml) cooled in an ice bath was added dropwise diethylamine (32.2 g, 0.44 mol) over 20 minutes. The reaction mixture was refluxed for 17 hours, cooled to room temperature and the solvent was stripped. The residue was dissolved in 1N NaOH (50 ml), extracted with ether (50-100 ml) and the aqueous layer was acidified with 2N HCl to a pH of 3. The aqueous layer was stripped and the residue was treated with ethanol, filtered and the ethanol was stripped. The residue was recrystallized from isopropyl alcohol (3×) to afford 13.54 g of 4-diethylaminomethyl benzoic acid hydrochloride, m.p. 189°-191° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 17 hours
  2. extractionextracted with ether (50-100 ml)
  3. additionthe residue was treated with ethanol
  4. filtrationfiltered
  5. customThe residue was recrystallized from isopropyl alcohol (3×)

Sources & evidence

ORD record
ord-4949b25ea9c648309f7cc2d57a6a4212
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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