4-(benzyloxy)-N-propylbutanamide → N-[4-(benzyloxy)butyl]-N-propylamine

HRID 348836Notes

Reaction equation

HRID 348836 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH3:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:14][CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 210859244-(benzyloxy)-N-propylbutanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 21087152N-[4-(benzyloxy)butyl]-N-propylamineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold, stirred mixture of 4-(benzyloxy)-N-propylbutanamide (2.59 g, 11.0 mmol) in THF (8 mL) is added lithium aluminum hydride (0.54 g, 14.3 mmol). The reaction mixture is heated to 40–50 degrees C. for 5 hours. The cooled reaction mixture is quenched with water (0.5 mL), sodium hydroxide (2 N, 1.0 mL), and saline (0.5 mL) then diluted with ether (30 mL). The precipitate that formed is filtered off, and the ether phase dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give N-[4-(benzyloxy)butyl]-N-propylamine (2.41 g), APCI-MS (m/z): 222 [M +H]+.

Workup

  1. temperatureThe reaction mixture is heated to 40–50 degrees C
  2. customThe cooled reaction mixture
  3. customis quenched with water (0.5 mL), sodium hydroxide (2 N, 1.0 mL), and saline (0.5 mL)
  4. additionthen diluted with ether (30 mL)
  5. customThe precipitate that formed
  6. filtrationis filtered off
  7. dry with materialthe ether phase dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44f38d7bfdb941658421ccfb55f08c29
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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