Triethylamine → HCID 21842387, compound

HRID 1386950Notes

Reaction equation

HRID 1386950 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.Cl.[CH3:14][NH:15][CH3:16].C(N(CC)CC)C>CCOCC>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:15]([CH3:16])[CH3:14])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 21842387HCID 21842387, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a cooled (−10° C.) solution of methyl-3-(bromomethyl)benzoate (22.9 g, 100 mmol) in ether (250 ml) was added dimethylamine hydrochloride salt (17.9 g, 220 mmol) followed by slow addition of triethylamine (30.6 ml, 220 mmol). The mixture was then allowed to warm to r.t. over 48 h, the solids were filtered off and the filter-cake washed with ether. The yellow oil remaining after evaporation of the solvent was distilled over a Vigreux column to afford the title compound (10.7 g, 55% yield) as a colorless oil. MS: m/e=193 (M+).

Workup

  1. filtrationthe solids were filtered off
  2. washthe filter-cake washed with ether
  3. customafter evaporation of the solvent
  4. distillationwas distilled over a Vigreux column

Sources & evidence

ORD record
ord-d6859fa57bb5424a83cce4348e337447
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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