Triethylamine → 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester

HRID 649046Notes

Reaction equation

HRID 649046 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])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.CN([CH:29]([CH3:33])[C:30]([OH:32])=[O:31])C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:6]([N:3]([CH2:33][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])[CH2:4][CH3:5])[CH3:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 126649942,3-Diethyl-4-methoxynaphtholHCID 216146742-Dimethylamino-propionic acid hydrochloride

Product 1

HCID 571098023-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl esterYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dry methylene chloride (30 ml) and triethylamine (0.33 ml, 2.34 mmole) are added to a mixture of 2,3-diethyl-4-methoxynaphthol (180 mg, 0.78 mmole), dimethylamino propionic acid hydrochloride (2 eq, 283 mg, 1.56 mmole), dicyclohexylcarbodiimide (2 eq, 322 mg, 1.56 mmole) and 4-dimethylaminpyridine (1 eq, 95 mg, 0.78 mmole) at room temperature under argon, and the resulting suspension is stirred at room temperature under argon for two days. The white precipitate is removed by filtration, and the filtrate is concentrated. Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane isolates 144 mg (51.8% ) of 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a colorless oil.

Workup

  1. customThe white precipitate is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. additionThick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane

Sources & evidence

ORD record
ord-eb61534544b34bdfb5b61227506f5515
Source dataset
uspto-grants-1988_04
Patent number
US04737519

Reaction notes

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