Potassium Cyanide → (+/-)3-(Dimethylamino)tetrahydro-3-furancarbonitrile

HRID 20823Notes

Reaction equation

HRID 20823 reaction equation
[O:1]1CCC(=O)C1.Cl.CNC.[C-]#N.[K+].[CH3:14][N:15]([CH3:23])[C:16]1([C:21]#[N:22])[CH2:20][CH2:19]C[CH2:17]1>O>[CH3:14][N:15]([CH3:23])[C:16]1([C:21]#[N:22])[CH2:20][CH2:19][O:1][CH2:17]1

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 5293923-OxotetrahydrofuranHCID 107730491-(Dimethylamino)cyclopentanecarbonitrile

Product 1

HCID 10630582(+/-)3-(Dimethylamino)tetrahydro-3-furancarbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound (6.54 g, 88%) was prepared from dihydro-3(2H)-furanone D44 (4.54 g, 0.053 mol), dimethylamine hydrochloride (4.9 g, 0.06 mol) and potassium cyanide (3.5 g, 0.054 mol) in water (100 ml) in a similar manner to that described in D1. 1H NMR (CDCl3) δ: 2.15 (1H, m), 2.33 (6H, s), 2.44 (1H, m), 3.69 (1H, d), 4.02-4.13 (2H, m), 4.17 (1H, m).

Sources & evidence

ORD record
ord-016a263677f94642b1a0aff980bd059e
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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