Pyridine → HCID 13560808, compound

HRID 1285555Notes

Reaction equation

C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:10][C:11]1[NH:12][C:13]([CH3:41])=[C:14]([C:32]([O:34]CCCN(C)C)=[O:33])[CH:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]=1[C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:18].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:10][C:11]1[NH:12][C:13]2[CH2:41][O:34][C:32](=[O:33])[C:14]=2[CH:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]=1[C:17]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[O:18]

Participants

Conditions

Temperature: -20 °C

Procedure

1.31 grams of 80 percent pyridinium bromide perbromide (3.28 millimoles) was added to a cooled to -20° C. solution of 1.30 grams (2.84 millimoles) of bis(3-dimethylaminopropyl) 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.4 milliliter of pyridine in 20 milliliters of chloroform. The resulting mixture was stirred at -20° C. for 1/2 hour and then heated at reflux for 2 hours. The mixture was cooled to room temperature and allowed to stir overnight. The crude product was chromatographed on silica gel with 1 percent methanol in chloroform saturated with ammonia as eluant to obtain 161 milligrams of an oil which crystallized when mixed with CDCl3 for NMR analysis. The product was concentrated in vacuo and recrystallized from ethyl acetate-hexane to obtain crystals of m.p. 112°-115° C. after drying 70° C. overnight. The product was a hydrate having elemental analyses as follows:

Workup

temperatureheated
temperatureat reflux for 2 hours
temperatureThe mixture was cooled to room temperature
stirringto stir overnight
customThe crude product was chromatographed on silica gel with 1 percent methanol in chloroform saturated with ammonia as eluant

Sources & evidence

ORD record: ord-3c2ab92565e244139c1b6259eb671af2
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04567268

Reaction notes

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