Hydrochloric Acid → 3-(p-(Dimethylamino)phenyl)propanol

HRID 2178275Notes

Reaction equation

HRID 2178275 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]([CH3:19])[C:9]1[CH:18]=[CH:17][C:12]([CH:13]=[CH:14][CH:15]=[O:16])=[CH:11][CH:10]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:19][N:8]([CH3:7])[C:9]1[CH:18]=[CH:17][C:12]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 922244-(Dimethylamino)-cinnamaldehydeHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 30208873-(p-(Dimethylamino)phenyl)propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (0.066 g, 1.71 mmol) was added to a solution of 4-(dimethylamino)cinnamaldehyde (0.10 g, 0.57 mmol) in anhydrous THF (2 mL). The reaction mixture was heated at reflux for 2 hours and cooled to rt. To the reaction mixture was added 1M HCl dropwise. The reaction mixture was stirred for 5 minutes before saturated NaHCO3 was added and the mixture was extracted with DCM. The organic phases were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of PE:EtOAc 2:1 to provide the desired product 3-(4-(dimethylamino)phenyl)propan-1-ol (48A).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. additionwas added
  4. extractionthe mixture was extracted with DCM
  5. dry with materialThe organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography on silica gel eluting with a gradient of PE

Sources & evidence

ORD record
ord-27f068002ae6453492dd10212ea0bec3
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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