Diethyl Ether → Bis(cyclopropylmethyl)amine

HRID 577784Notes

Reaction equation

HRID 577784 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:12]([NH:14][CH2:15][CH3:16])=O)[CH2:11][CH2:10]CC=1.[CH3:17][CH2:18]OCC>>[CH:16]1([CH2:15][NH:14][CH2:12][CH:7]2[CH2:11][CH2:10]2)[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 21226445Aluminium lithium hydrideHCID 55300846N-Ethylcyclopent-1-ene-1-carboxamide

Product 1

HCID 15284719Bis(cyclopropylmethyl)amineYield 69%

Procedure

To a suspension of lithium aluminum hydride (1.3 g, 9.35 mmol) in 10 mL dry ether, a solution of N-cyclopentenoyl-ethylamine (1.7 g, 13.3 mmol) in dry ether (10 mL) was added under a nitrogen atmosphere. This reaction was stirred at RT for 8 h and the reaction mixture was then quenched with saturated sodium sulfate solution, filtered, and the precipitate was washed with diethyl ether. The filtrate was concentrated to afford the title amine (0.8 g), yield: 69%.

Workup

  1. customthe reaction mixture was then quenched with saturated sodium sulfate solution
  2. filtrationfiltered
  3. washthe precipitate was washed with diethyl ether
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1c70a9d6b9e04616857ec57c28b49233
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

Loading…