Sodium Iodide → HCID 19834979, compound

HRID 477813Notes

Reaction equation

HRID 477813 reaction equation
[Cl:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.[CH2:16]([NH:23][CH3:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I-].[Na+]>CN(C)C=O>[ClH:1].[ClH:1].[CH2:16]([N:23]([CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1)[CH3:24])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 7669N-MethylbenzylamineHCID 28015624-Benzyl-2-(chloromethyl)morpholine

Product 1

HCID 19834979HCID 19834979, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 58 g of 2-chloromethyl-4-benzylmorpholine, 62.3 g of N-benzyl-N-methylamine and 38.6 g of sodium iodide in 220 ml of dimethylformamide is refluxed under stirring at 140° C. for 6 hours. After completion of the reaction, the dimethylformamide is distilled off under reduced pressure, water is added to the residue and the mixture is subjected to extraction with ethyl acetate. After washing with water, the resultant mixture is dried over anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. The residue is treated in 37% hydrochloric acid-ethanol to give 2-(N-benzyl-N-methylaminomethyl)-4-benzylmorpholine dihydrochloride as white crystals. The obtained hydrochloride compound (29.7 g) is subjected to catalytic reduction with 50 ml of ethanol, 80 ml of water and 3 g of 10% palladium-carbon. After absorbing the theoretical volume of the hydrogen, the catalyst is filtered off and the solvent of the filtrate is distilled off to give 2-(methylaminomethyl)morpholine dihydrochloride monohydrate as white crystals, melting at 122°-124° C.

Workup

  1. temperatureis refluxed
  2. customAfter completion of the reaction
  3. distillationthe dimethylformamide is distilled off under reduced pressure, water
  4. additionis added to the residue
  5. extractionthe mixture is subjected to extraction with ethyl acetate
  6. washAfter washing with water
  7. dry with materialthe resultant mixture is dried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. additionThe residue is treated in 37% hydrochloric acid-ethanol

Sources & evidence

ORD record
ord-28194f56d827464a9caf6d4bce8886c5
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

Loading…