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

HRID 1179027Notes

Reaction equation

HRID 1179027 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, 1,680 ml aqueous dimethylamine solution (40 wt. %), 303 g dimethylamine hydrochloride and 200 g potassium cyanide were added to 200 g 1,4-dioxa-spiro[4.5]decan-8-one and the mixture was stirred for approx. 65 hours. The white suspension obtained was extracted four times with 800 ml ether each time, the combined extracts were concentrated, the residue was taken up in approx. 500 ml methylene chloride and the phases were separated. The methylene chloride phase was dried over sodium sulfate, filtered and concentrated. 265 g 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile were obtained as a white solid.

Workup

  1. customThe white suspension obtained
  2. extractionwas extracted four times with 800 ml ether each time
  3. concentrationthe combined extracts were concentrated
  4. customthe phases were separated
  5. dry with materialThe methylene chloride phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7e0ecb18d28e4cb7bd9b1e5adfac04d1
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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