Hydrochloric Acid → 3-Benzyloxy-4-(3-hydroxypropyl)benzylamine

HRID 1985835Notes

Reaction equation

HRID 1985835 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH:17]=O)[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[C:20]([CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=[O:21].CC(C)([O-])C.[K+].Cl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH2:17][CH2:25][CH2:20][OH:21])[CH2:12][NH2:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromideHCID 189739062-Benzyloxy-4-cyanobenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 231438633-Benzyloxy-4-(3-hydroxypropyl)benzylamineYield 18.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzyloxy-4-formylbenzonitrile (0.93 g) and (carboethoxymethyl)triphenylphosphonium bromide (2.52 g) were suspended in N,N-dimethylformamide (10 mL). To the reaction mixture was added potassium t-butoxide (0.66 g), and the mixture was stirred at room temperature for 18 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (10 mL), and the mixture was added dropwise to a suspension of lithium aluminum hydride (0.20 g) in tetrahydrofuran (15 mL) under ice-cooling. The mixture was stirred at 60° C. for 2 hours. After mixture was cooled in an ice bath, and to the reaction mixture were added dropwise ethanol and water successively, and then added diethyl ether. To the reaction mixture was added anhydrous sodium sulfate, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (0.20 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in tetrahydrofuran (10 mL)
  6. additionthe mixture was added dropwise to a suspension of lithium aluminum hydride (0.20 g) in tetrahydrofuran (15 mL) under ice-
  7. temperaturecooling
  8. stirringThe mixture was stirred at 60° C. for 2 hours
  9. temperatureAfter mixture was cooled in an ice bath
  10. additionto the reaction mixture were added dropwise ethanol and water successively
  11. additionTo the reaction mixture was added anhydrous sodium sulfate
  12. customthe insoluble material was removed by filtration
  13. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-31193a59103941e099cb162cf48bffa9
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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