Dimethyl Sulfate → HCID 23342805, compound

HRID 27422Notes

Reaction equation

HRID 27422 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[CH3:10][O:11][S:12]([O:15]C)(=[O:14])=[O:13]>C(OCC)C>[CH3:10][O:11][S:12]([O-:15])(=[O:14])=[O:13].[CH3:10][O:9][C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N+:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 17369N-Methylcaprolactam

Product 1

HCID 23342805HCID 23342805, compoundYield 182.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Stir 190 g of N-methylcaprolactam and 189 g of dimethylsulfate for 3 hours at 80° C. Cool the resulting reaction mixture to ambient temperature before shaking it with diethyl ether and then freeing it from solvent residue in vacuo to obtain 346 grams (g) of 2-methoxy-1-methyl-4,5,6,7-tetrahydro-3H-azepinium methylsulfate as a light yellow oil. Add this oil, drop by drop, to a solution of 110 g of dimethylamine in 600 milliliters (ml) of benzene while stirring and boil the thus-prepared admixture under reflux for 90 minutes. Collect the heavy phase and extract it several times with diethyl ether. Concentrate the produced yellowish oil in vacuo to obtain 336 g (93% of theory) of the title compound.

Workup

  1. temperatureCool
  2. customthe resulting reaction mixture to ambient temperature

Sources & evidence

ORD record
ord-43f6644a51dd426abec28bc7c895b38e
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Reaction notes

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