Hydrochloric Acid → HCID 3029410, compound

HRID 903968Notes

Reaction equation

HRID 903968 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]([CH:13]1[O:18][CH2:17][C:16](=O)[N:15]([CH3:20])[C:14]1=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:32]>O1CCCC1>[ClH:32].[CH3:1][O:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][CH:6]([CH:13]1[O:18][CH2:17][CH2:16][N:15]([CH3:20])[CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 23458432HCID 23458432, compound

Product 1

HCID 3029410HCID 3029410, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.8 g of 2-[α-(2-methoxyphenoxy)-benzyl]-4-methyl-morpholin-3,5-dione in 40 ml of anhydrous tetrahydrofuran was added dropwise under stirring to a suspension of lithium aluminium hydride (1.9 g) in 35 ml of THF. The mixture was refluxed under stirring for 6 hours. Dropwise addition was then made at 0°-5° C. of 4.1 ml of 23% HCl and the whole was stirred at room temperature for 2 hours. The suspended solid was filtered and washed several times with THF. The combined filtrates were evaporated to dryness under reduced pressure. The residue was taken up with ethyl ether and 4 ml of 18% methanolic HCl was added. The amorphous hydrochloride precipitated which was washed several times with fresh ethyl ether. By filtration there was obtained 5.8 g of 2-[α-(2-methoxyphenoxy)-benzyl]-4-methyl-morpholine hydrochloride, melting point 67°-90° C. Yield 84%.

Workup

  1. temperatureThe mixture was refluxed
  2. additionDropwise addition
  3. stirringthe whole was stirred at room temperature for 2 hours
  4. filtrationThe suspended solid was filtered
  5. washwashed several times with THF
  6. customThe combined filtrates were evaporated to dryness under reduced pressure
  7. additionwas added
  8. customThe amorphous hydrochloride precipitated which
  9. washwas washed several times with fresh ethyl ether
  10. filtrationBy filtration there

Sources & evidence

ORD record
ord-85b8415e5093472ca41f9f46f4f0042e
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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