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

HRID 1600817Notes

Reaction equation

HRID 1600817 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-a90bcb4f00504f04ab44868373898af6
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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