Hydrochloric Acid → HCID 10910573, compound
Reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[CH3:13]O>>[Cl-:1].[C:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][NH3+:2])=[CH:12][CH:11]=1)([O:10][CH3:13])=[O:9]Participants
Procedure
Gaseous hydrochloric acid was hubled for 5 minutes through a suspension of 4-(aminomethyl)benzoic acid (20 mmol) in 100 mL of methanol, upon which it dissolved. After heating at reflux for 10 minutes a precipitate was formed which was filtered off and washed with diethyl ether to yield 2.5 g (12.4 mmols, 62%) of 4-carbomethoxy-benzylammonium chloride. A solution of 1.5 g of this compound in 10 mL ethanolamine was heated at 37° C. overnight. After removal of the solvent by vacuum destillation, the residue was dissolved in 300 mL water and treated with 50 g of Dowex H+ (SO3H). The resin was washed several times with water and 50% aq. methanol. Treatment of the resin with 5% aq. ammonia and yielded 1.0 g (5.15 mmol, 69%) of amine 7 as a yellow solid, m.p. 140°-143° C. A sample (approx. 100 mg) was further purified by preparative reverse-phase HPLC to give the pure trifluoroacetate salt as a colorless solid after lyophilyzation, the latter was used as cofactor.
Workup
- dissolutiondissolved
- temperatureAfter heating
- temperatureat reflux for 10 minutes a precipitate
- customwas formed which
- filtrationwas filtered off
- washwashed with diethyl ether
Sources & evidence
- ORD record
- ord-f1c273f8d4d548b89d3385e07f0e2ee3
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576174
Reaction notes
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