Aluminium lithium hydride → 2-(Cyclohepta-2,4,6-trien-1-yl)ethanamine

HRID 74751Notes

Reaction equation

HRID 74751 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:14][C:15]#[N:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=[CH:8]1>C(OCC)C>[CH:7]1([CH2:14][CH2:15][NH2:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=[CH:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 85933971Cyclohepta-2,4,6-trien-1-ylacetonitrile

Product 1

HCID 236233082-(Cyclohepta-2,4,6-trien-1-yl)ethanamineYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (911 mg, 24.0 mmol, 1.4 eq.) in anhydrous diethyl ether (75 mL, 0.23 M) at 0° C. was slowly added, drop-wise over 15 minutes, a solution of #61 (2.25 g, 17.2 mmol, 1 eq.) in diethyl ether (15 mL). The reaction was warmed to room temperature. After 5 hours, the reaction was cooled to 0° C. and quenched by addition of water (1 mL), then filtered through a small pad of Celite and washed with methanol. The filtrate was dried over sodium sulfate, filtered, and concentrated in vacuo to provide #62 (1.683 g, 73%) as a golden oil. LC-MS: m/z 136.1 [M+H+], retention time=0.23 minutes; 1H NMR (400 MHz, CDCl3) δ 6.64-6.67 (m, 2H), 6.16-6.21 (m, 2H), 5.16-5.21 (m, 2H), 2.84-2.89 (m, 2H), 1.86-1.92 (m, 2H), 1.62-1.70 (m, 1H).

Workup

  1. additionwas slowly added
  2. waitAfter 5 hours
  3. temperaturethe reaction was cooled to 0° C.
  4. customquenched by addition of water (1 mL)
  5. filtrationfiltered through a small pad of Celite
  6. washwashed with methanol
  7. dry with materialThe filtrate was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16f319f73b6d4d1eb1a927020cbe2e7b
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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