Ethylmorpholine → HCID 20079735, compound

HRID 1464143Notes

Reaction equation

HRID 1464143 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:17][NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:19](N1CCOCC1)C.CN(C1C=CC=CN=1)C.ClC(OCC(C)C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:17][NH:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

8

Reactant 6

HCID 7525EthylmorpholineHCID 218852-DimethylaminopyridineHCID 24436Sodium SulfateHCID 62365Isobutyl chloroformateHCID 75534455092-70-1HCID 21226445Aluminium lithium hydride

Product 1

HCID 20079735HCID 20079735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.73 g (0.031 mol) of 1-(3,4-dimethoxyphenyl)-1-cyclohexanemethanamine, 4.3 ml (0.00348 mol) of N-ethylmorpholine and 0.3 g of dimethylaminopyridine in 100 ml of abs. tetrahydrofuran was cooled to -10° and treated within 10 minutes with 4.4 ml (0.0348 mol) of isobutyl chloroformate. The mixture was then stirred at room temperature for 18 hours and filtered, and the solution was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and the organic solution was washed first with 1N hydrochloric acid and then with a saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated under reduced pressure. tetrahydrofuran and 2.35 g (0.062 mol) of lithium aluminium hydride and the mixture was heated to reflux for 2 hours, thereafter cooled and treated with a saturated sodium sulphate solution. After filtering the mixture and evaporating the solvent there was obtained an oil which was distilled at 153°/260 Pa, whereby there was obtained 1-(3,4-dimethoxyphenyl)-N-methyl- 1-cyclohexanemethanamine as a colourless oil which was used directly in the next step.

Workup

  1. filtrationfiltered
  2. customthe solution was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe organic solution was washed first with 1N hydrochloric acid
  5. dry with materialwith a saturated sodium bicarbonate solution, dried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. temperatureto reflux for 2 hours
  8. temperaturecooled
  9. filtrationAfter filtering the mixture
  10. customevaporating the solvent there
  11. customwas obtained an oil which
  12. distillationwas distilled at 153°/260 Pa

Sources & evidence

ORD record
ord-fed4a5641e7c4927b6ee60ee82923952
Source dataset
uspto-grants-1994_04
Patent number
US05302727

Reaction notes

Loading…