Hydrochloric Acid → (R)-1-(2-Methoxyphenyl)-4-[2-(methyl)-2-(2-pyridinylamino)ethyl]piperazine

HRID 566590Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH3:15][C@@H:16]1[CH2:20]OS(=O)(=O)[N:17]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.Cl>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([CH3:20])[NH:17][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:11][CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

9.16 grams (46.6 millimoles) of 1-(2-methoxyphenyl)piperazine in one portion was added under argon to a solution of 10 grams (46.6 millimoles) of (R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide in 200 millilitres of acetonitrile. The mixture became yellow. After ½ hour, the reaction mixture was heated to 50° C. for 1 hour and then stirred at room temperature overnight. Then dilute hydrochloric acid was added. The mixture was washed with ethyl acetate, basified to pH 12 and extracted twice with ethyl acetate. The organic phases were washed with brine, dried (Mg SO4) and subjected to evaporation to give 12.053 grams of the title compound which was purified by columning in the system ethyl ether/hexane (1:1) Al2O3 to afford 9.96 grams of the title compound.

Workup

washThe mixture was washed with ethyl acetate
extractionextracted twice with ethyl acetate
washThe organic phases were washed with brine
dry with materialdried (Mg SO4)
customsubjected to evaporation

Sources & evidence

ORD record: ord-218d6a16b8464257ab4e0adf70060ea1
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06175012B1

Reaction notes

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