Diethyl Ether → (4-Piperidinophenyl)methylamine

HRID 1505168Notes

Reaction equation

HRID 1505168 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCO[CH2:18][CH3:19]>>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([CH2:1][NH2:8])=[CH:3][CH:4]=2)[CH2:19][CH2:18][CH2:3][CH2:2][CH2:1]1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 7505BenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 2795551(4-Piperidinophenyl)methylamineYield 82%

Procedure

Benzonitrile 18m (1.2 g, 6.48 mmol) dissolved in 10 ml of ether was added dropwise at 0° C. to LiAlH4 (2 equiv., 493 mg) suspended in diethyl ether (40 ml). The mixture was stirred at room temperature for 24 hours. The reaction was quenched by addition of water and filtrated and the salts were washed with ether. The organic phase was separated, anhydrified and evaporated giving 1 g of an orange oil. Yield=82%. 1HNMR (DMSO, 200 MHz) δ 1.57 (6H, m), 3.06 (4H, m), 3.58 (2H, s), 6.84 (2H, d, J=8.6 Hz), 7.13 (2H, d, J=8.4 Hz), 7.33 (2H, bs).

Workup

  1. customThe reaction was quenched by addition of water
  2. filtrationfiltrated
  3. washthe salts were washed with ether
  4. customThe organic phase was separated
  5. customevaporated

Sources & evidence

ORD record
ord-af2b2109437a42668281f7bfc0c1af05
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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