Hydrochloric Acid → HCID 10801994, compound

HRID 863460Notes

Reaction equation

HRID 863460 reaction equation
[CH2:1]([N:8]([CH3:21])[C:9](=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.CO.Cl>O1CCCC1>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 3389163HCID 3389163, compound

Product 1

HCID 10801994HCID 10801994, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-benzyl-N-methyl-4-nitrophenylacetamide (step (b), 24.9 g, 87.6 mmol) in tetrahydrofuran (270 ml) under nitrogen, was added dropwise 1.0M borane-tetrahydrofuran (245 ml, 245 mmol). The reaction was heated at reflux for 2 hours, cooled, then methanol (53 ml) was added dropwise followed by the cautious addition of aqueous 2.5N hydrochloric acid (100 ml). The resulting mixture was refluxed for 1 hour and then concentrated on a rotary evaporator to remove the organic solvents. Water was added to the residue and the mixture was basified to pH 11 with 2.5N aqueous sodium hydroxide. The product was then extracted into three portions of methylene chloride. The combined extracts were washed with water, dried over magnesium sulfate, filtered and concentrated to yield 23.7 g (100%) of N-benzyl-N-methyl[2-(4-nitrophenyl)ethyl]amine. The hydrochloride salt, prepared in methanol and recrystallized from 95% ethanol-ether, melted at 222°-4° C. (dec).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. temperatureThe resulting mixture was refluxed for 1 hour
  5. concentrationconcentrated on a rotary evaporator
  6. customto remove the organic solvents
  7. additionWater was added to the residue
  8. extractionThe product was then extracted into three portions of methylene chloride
  9. washThe combined extracts were washed with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a147ab2ea5764ffda4bd1a2cf6bd4ada
Source dataset
uspto-grants-1998_02
Patent number
US05721247

Reaction notes

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