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a N-(3-carbomethoxyphenyl)-2-hydroxy-5-carbomethoxybenzamide STR28 Methyl 4-hydroxyisophthalate (1.0 g) and oxalyl chloride (2.2 ml) were stirred together for 18 h in dry dichloromethane containing one drop of dimethylformamid. Removal of solvent gave a white solid which was dissolved in dichloromethane (30 ml) and added to a solution of methyl 3-aminobenzoate (0.8 g) in dichloromethane (30 ml) and pyridine (6.1 ml) at 0° C. After 18 h this was poured into dilute hydrochloric acid and extracted to give a yellow foam (1.7 g). 1 H-NMR (CDCl3) delta: 3.84 (6H,s), 6.8-8.8 (7H,m), 10.7 (2H,br).
N-(tertiary)-butylamine-glyoxalbisaldimine[ No CAS ]
[ 613-73-0 ]
[ 3029-30-9 ]
Yield
Reaction Conditions
Operation in experiment
68.5%
EXAMPLE 2 15.6 Grams (0.1 mole) of o-phenylene-diacetonitrile, 20.1 g (0.1 mole) of N-(tertiary)-butylamine-glyoxalbisaldimine and 50 ml of dimethyl-formamide were heated at 130 C. for 1 hour, while stirring, and the stirring was continued for 3 to 4 hours at a temperature of from 130 to 135 C. In the course of this process 16 ml of tertiary butylamine (corresponding to 83.5% of reacted aldimine) were distilled off. After the reaction mixture had been cooled to 10 C. to 20 C., the crystal paste formed was suction-filtered, was washed with cold methanol and dried. Yield: 12 g of 1,4-naphthodinitrile (68.5% of the theory). Melting point: 209 C.
0.341 g of 60percent NaH in oil is added to a solution of 0.748 g of N-methylacetamide in 80 ml of THF and stirred for 10 minutes at RT. Then 2 g of <strong>[655225-01-7]tert-butyl 4-(2-bromoethyl)piperazinecarboxylate</strong> is added and stirred for 16 hours at RT. Water is added to the reaction mixture, it is decanted and the organic solvent is evaporated under vacuum. The residue is dissolved in DCM, filtered through a Chem Elut.(R). cartridge, eluting with DCM and the solvents are evaporated under vacuum. The residue is purified by preparative HPLC and a white solid is obtained.
Preparation 7.3N-Methyl-N-[2-(piperazin-1 -yl)ethyl]acetamide ditrifluoroacetate. 0.341 g of 60percent NaH in oil is added to a solution of 0.748 g of N- methylacetamide in 80 ml of THF and stirred for 10 minutes at RT. Then 2 g of fe/f-butyl 4-(2-bromoethyl)piperazinecarboxylate is added and stirred for 16 hours at RT. Water is added to the reaction mixture, it is decanted and the organic solvent is evaporated under vacuum. The residue is dissolved in DCM, filtered through a Chem Elut.(R). cartridge, eluting with DCM and the solvents are evaporated under vacuum. The residue is purified by preparative HPLC and a white solid is obtained. The solid is dissolved in 5 ml of DCM, 1 .2 ml of TFA is added and it is stirred for 16 hours at RT. The reaction mixture is diluted by adding 100 ml of toluene and the solvents are concentrated under vacuum.1 .5 g of the expected compound is obtained.
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