Dimethyl Sulfoxide → HCID 21436250, compound

HRID 1283987Notes

Reaction equation

HRID 1283987 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][CH:9]2[C:14](=[C:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][CH2:11][NH:10]2)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.F[C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1>O>[N+:37]([C:34]1[CH:35]=[CH:36][C:31]([N:10]2[CH2:11][CH2:12][CH2:13][C:14](=[C:15]([CH3:17])[CH3:16])[CH:9]2[CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:19][CH:18]=2)=[CH:32][CH:33]=1)([O-:39])=[O:38]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 21436291HCID 21436291, compound

Product 1

HCID 21436250HCID 21436250, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g. of 2-(p-methoxybenzyl)-3-isopropylidenepiperidine hydrochloride, 1.1 g. of powdered potassium carbonate, 10 ml. of dimethyl sulfoxide, and 0.4 ml. of p-fluoronitrobenzene was stirred and heated on a steam bath for 1 hour. The reaction mixture was then poured into water and the water was decanted from the precipitated gum. The gum was washed with several portions of water and then taken up in diethyl ether, and the ether was washed with several portions of water. The ether was dried and filtered, and the filtrate was evaporated to dryness under reduced pressure to yield 1-(p-nitrophenyl)-2-(p-methoxybenzyl)-3-isopropylidenepiperidine as a residue. Neither the residue nor its hydrochloride could be induced to crystallize, although only one component could be observed on thin layer chromatographic analysis using several developing systems on both silica gel and alumina. The nuclear magnetic resonance spectrum (CDCl3) of the crude residue showed: 439 (A2B2), 410, (A2B2), 295 (t,1,J=7 cps), 222 (a,3), 172 (d,2, J=7 cps), 95, (s,3), 76 (d,3,J=1-2 cps). The ultraviolet spectrum (95% ethanol) showed: 272s (ε4100), 286s (ε3500), 400 m (ε16300); lit, p-methylanisole 277 (ε2100), 284 (ε1800); N,N-dimethyl-p-nitroaniline 395 (ε20000).

Workup

  1. additionA mixture of 1.0 g
  2. temperatureheated on a steam bath for 1 hour
  3. customthe water was decanted from the precipitated gum
  4. washThe gum was washed with several portions of water
  5. washthe ether was washed with several portions of water
  6. dry with materialThe ether was dried
  7. filtrationfiltered
  8. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-59c2ba3ceea2404f897bf05d691896de
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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