Dimethyl Sulfate → HCID 19387890, compound

HRID 1757446Notes

Reaction equation

HRID 1757446 reaction equation
[NH2:1][CH:2]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)[CH3:3].S(OC)(O[CH3:18])(=O)=O.[O-2].[Mg+2]>C1(C)C=CC=CC=1>[NH2:1][CH:2]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[CH3:18])=[CH:6][CH:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 6850729Magnesium monoxideHCID 19387883HCID 19387883, compound

Product 1

HCID 19387890HCID 19387890, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Example P-13:1.3 g of 7-(1-aminoethyl)-1,2,3,4-tetrahydro-quinoline, 0.73 gof dimethyl sulfate and 0.27 g of ground magnesium oxide in 50 ml of absolute toluene are placed in a sulfonation flask. The internal temperature is then increased to 100°-105° C. and the mixture is stirred at that temperature for 18 hours. After cooling, inorganic material is filtered off, 10 ml of cone. HCl are added to the toluene solution, and the batch is maintained at 70° C. for 2 hours. The batch is then neutralised with sodium hydroxide solution and the organic phase is removed. The aqueous phase is subsequently further extracted twice with ethyl acetate and the organic phases are dried over Na2SO4. After removal of the solvent under a water-jet vacuum, 1.2 g of crude product are obtained which can be purified by flash chromatography on silica gel (eluant: ethyl acetate/n-hexane 1: 1) to yield 1.05 g of 7-(1-aminoethyl)-1-methyl-1,2,3,4-tetrahydro-quinoline in the form of a red oil (1H-NMR).

Workup

  1. temperatureThe internal temperature is then increased to 100°-105° C.
  2. temperatureAfter cooling
  3. filtrationinorganic material is filtered off
  4. additionHCl are added to the toluene solution
  5. customthe organic phase is removed
  6. extractionThe aqueous phase is subsequently further extracted twice with ethyl acetate
  7. dry with materialthe organic phases are dried over Na2SO4
  8. customAfter removal of the solvent under a water-jet vacuum, 1.2 g of crude product
  9. customare obtained which
  10. customcan be purified by flash chromatography on silica gel (eluant: ethyl acetate/n-hexane 1: 1)

Sources & evidence

ORD record
ord-4bcfe809a544425a91f35a279d14ac7d
Source dataset
uspto-grants-1995_08
Patent number
US05446040

Reaction notes

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