Triethylamine → N,N-dimethylamino acetic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester

HRID 649047Notes

Reaction equation

HRID 649047 reaction equation
C(N(CC)CC)C.[CH2:8]([C:10]1[C:19]([CH2:20][CH3:21])=[C:18]([O:22][CH3:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1O)[CH3:9].Cl.[CH3:26][N:27]([CH2:29][C:30]([OH:32])=[O:31])[CH3:28]>C(Cl)Cl>[CH3:26][N:27]([CH2:29][C:30]([O:32][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]([O:22][CH3:23])=[C:19]([CH2:20][CH3:21])[C:10]=1[CH2:8][CH3:9])=[O:31])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 126649942,3-Diethyl-4-methoxynaphthol

Product 1

HCID 23161585N,N-dimethylamino acetic acid, 2,3-diethyl-4-methoxynaphth-1-yl esterYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (3 eq) and dry methylene chloride (150 ml) are introduced to a mixture of 2,3-diethyl-4-methoxynaphthol (1.59 g, 6.5 mmole), dimethylamino acetic acid hydrochloride (2 eq, 1.8 g, 13.0 mmole), dicyclohexylcarbadiimide (2 eq, 2.7 g, 13.0 mmole) and 4-dimethylaminpyridine (1 eq, 2.7 ml, 19.5 mmole), prepared under an argon atmosphere, at room temperature under argon. The resulting suspension is stirred at room temperature for 20 hours under argon, then diluted with 300 ml of methylene chloride. The methylene chloride extracts are washed thoroughly with saturated aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is chromatographed through a silica gel (200 g) flash column and eluted by ether to give 1.48 g (72.2%) of N,N-dimethylamino acetic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a yellowish brown oil.

Workup

  1. customprepared under an argon atmosphere, at room temperature under argon
  2. washThe methylene chloride extracts are washed thoroughly with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through a silica gel (200 g) flash column
  7. washeluted by ether

Sources & evidence

ORD record
ord-9325f36e28e24f3892c439f8942e9309
Source dataset
uspto-grants-1988_04
Patent number
US04737519

Reaction notes

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