Lithium → 2-Methyl-2-(thien-3-yl)propylamine

HRID 1258055Notes

Reaction equation

HRID 1258055 reaction equation
[CH3:1][C:2]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)([CH3:5])[C:3]#[N:4].[Li]>CCOCC>[CH3:1][C:2]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)([CH3:5])[CH2:3][NH2:4]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 68959143157763-70-7

Product 1

HCID 667224312-Methyl-2-(thien-3-yl)propylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-methyl-2-thiophen-3-yl-propionitrile in anhydrous ether (200 mL) was added lithium aluminumhydride (5.7 g, 3 equiv) at 0° C. under nitrogen. Stirring was continued for 0.5 h at 20° C. and 3 h at reflux under nitrogen. After cooling, it was quenched with 10% aqueous Rochelle's salt (Yamada, F. et al. Heterocycles, 1998, 49:451-457) and the solid was removed with filtration and washed with ether. The combined filtrate was washed with water and dried over MgSO4. Evaporation of solvent afforded 2-methyl-2-thiophen-3-yl-propylamine as an oil (4.62 g). 1H-NMR(CDCl3): δ 7.29 (1H, dd), 7.03 (1H, dd), 6.99 (1H, dd), 2.74 (2H, s), 1.29 (6H, s).

Workup

  1. temperatureat reflux under nitrogen
  2. temperatureAfter cooling
  3. customit was quenched with 10% aqueous Rochelle's salt (Yamada, F. et al. Heterocycles, 1998, 49:451-457)
  4. customthe solid was removed with filtration
  5. washwashed with ether
  6. washThe combined filtrate was washed with water
  7. dry with materialdried over MgSO4
  8. customEvaporation of solvent

Sources & evidence

ORD record
ord-43eabf29438e40f2b21e38e263fe316c
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

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