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

HRID 1350995Notes

Reaction equation

HRID 1350995 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-c62d696519c84a309479e54eb176f268
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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