Ethylmorpholine → HCID 20079735, compound

HRID 1654156Notes

Reaction equation

HRID 1654156 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. The residual oil was treated with 100 ml of abs. 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. additionThe residual oil was treated with 100 ml of abs
  8. temperatureto reflux for 2 hours
  9. temperaturecooled
  10. filtrationAfter filtering the mixture
  11. customevaporating the solvent there
  12. customwas obtained an oil which
  13. distillationwas distilled at 153° /260 Pa

Sources & evidence

ORD record
ord-97d29894206341a38c380ced49d8ab08
Source dataset
uspto-grants-1995_04
Patent number
US05405866

Reaction notes

Loading…