Methylamine → Hydrochloric Acid

HRID 978482Notes

Reaction equation

HRID 978482 reaction equation
[ClH:1].C[O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[CH2:21][CH2:20][O:19][CH:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17]2)[CH3:15])=[CH:9][CH:8]=1.[CH3:29][NH2:30].CO.C(OCC)(=O)C.C(OCC)C>CO>[ClH:1].[ClH:1].[C:22]1([CH:18]2[CH2:17][N:16]([CH:14]([CH3:15])[CH2:13][C:10]3[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([NH:30][CH3:29])=[O:3])=[CH:8][CH:9]=3)[CH2:21][CH2:20][O:19]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 6329Methylamine3×HCID 13851158HCID 13851158, compoundHCID 21879645HCID 21879645, compound

Product 2

HCID 313Hydrochloric AcidHCID 70381892HCID 70381892, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[2-(2-phenylmorpholino)propyl]phenoxyacetic acid methyl ester hydrochloride (3.0 g; obtained from the mother liquors of Example 1) in methanol (50 ml) was added a 30% aqueous solution of methylamine (10 ml). This mixture was heated under reflux for 3 hours during which time 3 further 10 ml portions of the methylamine solution were added. The solution was cooled to room temperature, a further 10 ml portion of methylamine solution added, and the reaction mixture allowed to stand at room temperature overnight. The solvent was removed under vacuum, aqueous sodium carbonate added to the residue and extracted with dichloromethane (X2). The combined extracts were washed with brine (X2), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated to dryness. Chromatography of the residue on silica gel in 2% methanol-dichloromethane gave an oil, which, on treatment with an ethereal solution of hydrogen chloride, gave the title compound, m.p. 127°-130° C. (methanol-ethyl acetate-diethyl ether), as a 12:88 mixture of diastereoisomers.

Workup

  1. temperatureThis mixture was heated
  2. additionwere added
  3. customThe solvent was removed under vacuum, aqueous sodium carbonate
  4. additionadded to the residue
  5. extractionextracted with dichloromethane (X2)
  6. washThe combined extracts were washed with brine (X2)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customthe filtrate evaporated to dryness
  10. customChromatography of the residue on silica gel in 2% methanol-dichloromethane gave an oil, which

Sources & evidence

ORD record
ord-39f2b3e5d82542faae27f94dc6bda7ae
Source dataset
uspto-grants-1987_05
Patent number
US04665072

Reaction notes

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