Water → 3,3,3-trifluoro-N2-(4-methoxybenzyl)-2-methylpropane-1,2-diamine

HRID 444945Notes

Reaction equation

HRID 444945 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)([CH3:6])[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[F:1][C:2]([F:17])([F:18])[C:3]([CH3:6])([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:4][NH2:5]

Participants

5

Reactant 3

HCID 962Water2×HCID 21226445Aluminium lithium hydrideHCID 866576713,3,3-Trifluoro-2-(4-methoxybenzylamino)-2-methyl propanenitrile

Product 1

HCID 584423453,3,3-trifluoro-N2-(4-methoxybenzyl)-2-methylpropane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 3,3,3-trifluoro-2-(4-methoxybenzylamino)-2-methyl propanenitrile (1.5 g, 5.81 mmol) in dry diether ether (50 ml) was added LiAlH4 (11.62 ml of a 2M solution in THF) and the resulting mixture was stirred at RT overnight. The reaction mixture was hydrolyzed by successive addition of water 15% KOH, and water. The resulting precipitate was filtered on Celite® (filter material) and the organic portion was washed with water, dried over MgSO4 and concentrated under reduced pressure to afford the title product; 1H NMR (400 MHz, Methanol-d4) δ 7.97 (1H, s), 7.85 (1H, s), 7.60 (1H, s), 3.97 (3H, s), 3.77 (1H, m), 3.56 (1H, m), 1.37 (3H, s)

Workup

  1. filtrationThe resulting precipitate was filtered on Celite® (filter material)
  2. washthe organic portion was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ec727423f674508969b909f189a2e70
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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