Dimethylamine → 8-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

HRID 890609Notes

Reaction equation

HRID 890609 reaction equation
[CH3:1][NH:2][CH3:3].Cl.[CH3:5][NH:6]C.[C-]#N.[K+].[O:11]1[C:15]2([CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1>CO>[CH3:1][N:2]([CH3:3])[C:18]1([C:5]#[N:6])[CH2:19][CH2:20][C:15]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 ml methanol, 1680 ml aqueous dimethylamine solution (40 m %), 303 g dimethylamine hydrochloride and 200 g potassium cyanide were added to 200 g 1,4-dioxaspiro[4.5]decan-8-one and stirred for approximately 65 hours. The resulting white suspension was extracted four times with 800 ml ether each time, the combined extracts concentrated to low volume, the residue taken up in approximately 500 ml dichloromethane and the phases separated. The organic phase was dried over sodium sulfate, filtered and concentrated to low volume. 265 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile were obtained as a white solid.

Workup

  1. extractionThe resulting white suspension was extracted four times with 800 ml ether each time
  2. concentrationthe combined extracts concentrated to low volume
  3. customthe phases separated
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-f65598287d6f4d98a7aa275455a808ea
Source dataset
uspto-grants-2006_02
Patent number
US06998409B2

Reaction notes

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