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IdentificationBack Directory
[Name]

4-(1-AMINO-ETHYL)-BENZOIC ACID METHYL ESTER
[Synonyms]

Methyl 4-(1-aMinoethyl)benzoate
4-(1-AMINO-ETHYL)-BENZOIC ACID METHYL ESTER
Benzoic acid, 4-(1-aminoethyl)-, methyl ester
[MDL Number]

MFCD11505984
[MOL File]

80051-07-6.mol
Chemical PropertiesBack Directory
[Appearance]

Colorless to off-white Solid-liquid mixture
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

4-(1-AMINO-ETHYL)-BENZOIC ACID METHYL ESTER(80051-07-6)1HNMR
Hazard InformationBack Directory
[Synthesis]

METHYL 4-ACETYLBENZOATE

3609-53-8

Methylamine hydrochloride

593-51-1

Methylamine

74-89-5

4-(1-AMINO-ETHYL)-BENZOIC ACID METHYL ESTER

80051-07-6

GENERAL STEPS: Methyl 4-acetylbenzoate (1.07 g, 6 mmol), methylamine (33% ethanol solution, 4.5 mL), methylamine hydrochloride (1.62 g, 24.0 mmol), and sodium cyanoborohydride (0.56 g, 9.0 mmol) were dissolved in a solvent mixture of tetrahydrofuran (12 mL) and methanol (7 mL). The reaction mixture was stirred at 65 °C for 16 hours. Upon completion of the reaction, the reaction solution was concentrated in vacuum and the residue was redissolved in dichloromethane (20 mL) and washed with deionized water (20 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuum to give the crude methyl 4-(1-aminoethyl)benzoate, which could be used in the next reaction without further purification. Yield: 0.86 g, 75% yield. LCMS analysis (Method B): retention time 0.98 min, purity 89%; m/z 194.05 ([M+H]+, 100%).

[References]

[1] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 169-170
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