Dimethyl Sulfate → HCID 19849677, compound

HRID 1607882Notes

Reaction equation

HRID 1607882 reaction equation
O=C1C=CNCC1.C(Br)C=C.[C:12](=[O:15])([O-])[O-].[K+].[K+].[CH2:18]([N:21]1[CH:26]=[CH:25][C:24](=O)[CH2:23][CH2:22]1)[CH:19]=[CH2:20].C(N1CCC(=O)CC1)C=C.[CH3:38][O:39][S:40]([O:43]C)(=[O:42])=[O:41]>CC(C)=O.C(Cl)(Cl)Cl>[CH3:38][O:39][S:40]([O-:43])(=[O:42])=[O:41].[CH2:18]([N+:21]1[CH2:26][CH2:25][C:24]([O:15][CH3:12])=[CH:23][CH:22]=1)[CH:19]=[CH2:20]

Participants

9

Reactant 6

HCID 6497Dimethyl SulfateHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 113440581-(Prop-2-en-1-yl)piperidin-4-oneHCID 122236384(1H)-Pyridinone, 2,3-dihydro-HCID 16060802HCID 16060802, compound

Product 1

HCID 19849677HCID 19849677, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent2×

Procedure

The starting material was obtained as follows. Reaction of 1,2,3,4-tetrahydro-4-oxopyridine with 2 equivalents of allyl bromide and potassium carbonate in acetone under reflux for 15 hours gave, after purficiation by silica gel/EtOAc chromatography, 1,2,3,4,-tetrahydro-1-allyl-4-oxopyridine, nmr in CHCl3 :-2.5 tetrahydro-1-allyl4-oxopyridine, nmr in CHCl3 :-2.5 (t,2H); 3.46(t,2H); 3.8(d,2H); 5.0(d,1H); 5.24(m,1H); 5.4(m,1H); 5.4(m,1H); 5.8(m,1H); 7.06(d,1H). Reaction of this compound with dimethylsulphate at ambient temperature for 18 hours gave 1-allyl-2,3-dihydro-4-methoxypyridineium methyl sulphate. nmr in CDCl3 :-2.86(t,2H); 3.68(s,3H); 3.94(t,2H0; 3.96(s,3H); 4.5 (d,2H); 5.4(d,1H); 5.56(d,2H); 5.8(d,1H); 5.9(m,1H); 8.62(d,1H0.

Workup

  1. customThe starting material was obtained
  2. temperatureunder reflux for 15 hours
  3. customgave

Sources & evidence

ORD record
ord-9731c312e5294d089b5abd4d6a4f868a
Source dataset
uspto-grants-1989_09
Patent number
US04868173

Reaction notes

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