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

HRID 2244480Notes

Reaction equation

HRID 2244480 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:12][NH:13][CH3:14].[C-]#N.[K+].Cl.[CH3:19][NH:20]C>CO>[CH3:12][N:13]([CH3:14])[C:8]1([C:19]#[N:20])[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]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 g 1,4-dioxaspiro[4.5]decan-8-one were initially introduced into the reaction vessel, 1.68 l aqueous dimethylamine solution (40 per cent by volume), 200 ml methanol, 200 g potassium cyanide and 303 g dimethylamine hydrochloride were added in succession and the reaction mixture was stirred for 65 hours at room temperature. The white suspension obtained was extracted four times with 800 ml diethyl ether each time, the combined extracts were first concentrated and the residue was taken up in 500 ml methylene chloride, the organic phase was separated, dried over sodium sulfate, filtered and concentrated and the residue was largely freed from solvent residues in vacuo. 265 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile were obtained as a white solid.

Workup

  1. additionwere added in succession
  2. customThe white suspension obtained
  3. extractionwas extracted four times with 800 ml diethyl ether each time
  4. concentrationthe combined extracts were first concentrated
  5. customthe organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-08ce5d077465403ba9e855b28fe6a577
Source dataset
uspto-grants-2010_03
Patent number
US07678834B2

Reaction notes

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