Diethyl Ether → Bis(cyclopropylmethyl)amine

HRID 1911749Notes

Reaction equation

HRID 1911749 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-47a0511f35114441a80954781d73e038
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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