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

HRID 14042Notes

Reaction equation

HRID 14042 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

Conditions

Temperature
45 °C

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

Sources & evidence

ORD record
ord-a3d32cd58ed24db08438bf084793ed65
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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