Water → HCID 15572626, compound

HRID 1679978Notes

Reaction equation

HRID 1679978 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]([CH:14]1[O:19][CH2:18][CH2:17][NH:16][CH2:15]1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[CH:31](Cl)(Cl)Cl>[OH-].[Na+].C(OCC)C>[CH3:31][N:16]1[CH2:17][CH2:18][O:19][CH:14]([CH:6]([O:5][C:4]2[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=2[O:2][CH3:1])[C:7]2[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[CH2:15]1

Participants

7

Reactant 4

HCID 962Water2×HCID 6212ChloroformHCID 3029357HCID 3029357, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15572626HCID 15572626, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[α-(2-methoxy-phenoxy)-4-chloro-benzyl]-morpholine (7.35 g) in CHCl3 (50 ml), 2 N NaOH (18.2 ml) was added; the mixture was cooled to 0° C. and ethyl chloroformiate (3.5 ml) was dropped over 30 minutes. Stirring and cooling at 0° C. was maintained for 1 hour; the organic phase was separated, washed with water and dried over anhydrous CaCl2. The evaporation to dryness of the solvent gave a colourless oil which was dissolved in diethyl ether (100 ml) and added, at room temperature, to a suspension of LiAlH4 (2.5 g) in anhydrous diethyl ether (200 ml). The mixture was stirred at room temperature for 20 hours; water (2.5 ml), 15% NaOH (2.5 ml) and water (7.5 ml) were added. After filtration, the ethereal layer was separated and the aqueous phase was extracted with diethyl ether. The combined organic phases were washed with water and dried over anhydrous Na2SO4. After evaporation to dryness of the solvent, 4-methyl-2-[α-(2-methoxy-phenoxy)-4-chloro-benzyl]-morpholine was obtained as oil (6.25 g; yield 82%).

Workup

  1. additionethyl chloroformiate (3.5 ml) was dropped over 30 minutes
  2. temperaturecooling at 0° C.
  3. temperaturewas maintained for 1 hour
  4. customthe organic phase was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous CaCl2
  7. customThe evaporation to dryness of the solvent
  8. customgave a colourless oil which
  9. stirringThe mixture was stirred at room temperature for 20 hours
  10. filtrationAfter filtration
  11. customthe ethereal layer was separated
  12. extractionthe aqueous phase was extracted with diethyl ether
  13. washThe combined organic phases were washed with water
  14. dry with materialdried over anhydrous Na2SO4
  15. customAfter evaporation to dryness of the solvent

Sources & evidence

ORD record
ord-e9a888627b794bf88f6c522c3e2b4ff9
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

Loading…