Methoxyacetic Acid → HCID 70454348, compound

HRID 1249176Notes

Reaction equation

HRID 1249176 reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH2:5][C:6](O)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([CH:20]([NH2:25])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[OH-].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]\[C:31]([OH:33])=[O:32]>C1(C)C=CC=CC=1.CCOCC.O>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]\[C:31]([OH:33])=[O:32].[CH3:3][O:4][CH2:5][CH2:6][NH:25][CH:20]([C:16]1([C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=2)[CH2:17][CH2:18][CH2:19]1)[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

9

Reactant 5

HCID 12251Methoxyacetic AcidHCID 14798Sodium HydroxideHCID 134772DidesmethylsibutramineHCID 444266Maleic AcidHCID 4311764Sodium borohydride

Product 1

HCID 70454348HCID 70454348, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

Sodium borohydride (2.5 g) was added portionwise to a stirred solution of methoxyacetic acid (26.4 g) in toluene (300 ml) under an atmosphere of nitrogen and stirring was continued for 16 hours. A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (5 g) in toluene (50 ml) was then added and the mixture was heated under reflux with stirring for 24 hours. After cooling the reaction mixture, water (200 ml) was added and the mixture was basified with 16N aqueous sodium hydroxide solution. The product was extracted into ether and the extracts were washed with water, dried and evaporated to give a brown oil which was dissolved in ether (30 ml). A solution of maleic acid (4.8 g) in ether (250 ml) was added. The solid which precipitated was collected, dried and recrystallised from ethyl acetate with hot filtering to give N-(2-methoxyethyl)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine maleate (m.p. 131°-133° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. stirringwith stirring for 24 hours
  4. additionwas added
  5. extractionThe product was extracted into ether
  6. washthe extracts were washed with water
  7. customdried
  8. customevaporated
  9. customto give a brown oil which
  10. customThe solid which precipitated
  11. customwas collected
  12. customdried
  13. customrecrystallised from ethyl acetate
  14. filtrationwith hot filtering

Sources & evidence

ORD record
ord-f21880ca2c794884b34b0a0020fce694
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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