2,6-Dimethylmorpholine → HCID 13559067, compound

HRID 1761849Notes

Reaction equation

HRID 1761849 reaction equation
CS([CH2:5][CH:6]([CH3:18])[CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)(=O)=O.[CH3:19][CH:20]1[O:25][CH:24]([CH3:26])[CH2:23][NH:22][CH2:21]1>O>[CH3:26][CH:24]1[O:25][CH:20]([CH3:19])[CH2:21][N:22]([CH2:5][CH:6]([CH3:18])[CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH2:23]1

Participants

4

Reactant 2

HCID 1108622,6-DimethylmorpholineHCID 53881201HCID 53881201, compound

Product 1

HCID 13559067HCID 13559067, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.8 g (0.04 mol) of 1-methanesulphonyl-2-methyl-3-β-naphthylpropane and 9 g (0.078 mol) of 2,6-dimethylmorpholine are stirred at a bath temperature of 140° C. for 15 hours. Water is added to the resulting reaction mixture and the mixture is extracted several times with ether. The combined organic phases are dried over sodium sulphate and freed from the solvent in vacuo; the oily residue is purified by column chromatography (silica gel 60, petroleum ether/ethyl acetate=2:1). 6.2 g (52% of theory) of 1-(2,6-dimethylmorpholin-4-yl)-2-methyl-3-β-naphthyl-propane of refractive index nD20 =1.5527 are obtained.

Workup

  1. extractionthe mixture is extracted several times with ether
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. customthe oily residue is purified by column chromatography (silica gel 60, petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-28e146e8cb02498c8f39b26cf4f3bf6c
Source dataset
uspto-grants-1989_05
Patent number
US04829063

Reaction notes

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