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

HRID 1349385Notes

Reaction equation

HRID 1349385 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 of methanol, 1680 ml of aqueous dimethylamine solution (40 percent by weight), 303 g of dimethylamine hydrochloride and 200 g of potassium cyanide were added to 200 g of 1,4-dioxa-spiro[4.5]decan-8-one, and stirring was carried out for about 65 hours. The resulting white suspension was extracted four times using 800 ml of ether each time, the combined extracts were concentrated, the residue was taken up in about 500 ml of dichloromethane and the phases were separated. The dichloromethane phase was dried over sodium sulfate, filtered and concentrated. 265 g of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile were obtained in the form of a white solid.

Workup

  1. extractionThe resulting white suspension was extracted four times
  2. concentrationthe combined extracts were concentrated
  3. customthe phases were separated
  4. dry with materialThe dichloromethane phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fcab8f5756384db3b86a3136c108984a
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

Loading…