Hydrochloric Acid → Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrile

HRID 1821637Notes

Reaction equation

HRID 1821637 reaction equation
[CH3:1][NH:2][CH3:3].[O:4]1[C:8]2([CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]2)[O:7][CH2:6][CH2:5]1.[C-:16]#[N:17].[K+].Cl>CO>[CH3:1][N:2]([CH:14]([CH:11]1[CH2:10][CH2:9][C:8]2([O:4][CH2:5][CH2:6][O:7]2)[CH2:13][CH2:12]1)[C:16]#[N:17])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 9032Potassium CyanideHCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehyde

Product 1

HCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40% aqueous dimethylamine solution (85 ml, 0.67 mole), 1,4-dioxa-spiro-[4.5]decane-8-carbaldehyde 11 (240 g, 0.141 mole) and potassium cyanide (22.05 g, 0.338 mole) were added dropwise to a mixture of 4N hydrochloric acid (37 ml) and methanol (22 ml) while cooling with ice. The mixture was stirred for 4 days at room temperature and was then extracted with diethyl ether (4×100 ml) after adding water (80 ml). The organic phase was dried over sodium sulfate, concentrated by evaporation in vacuo, and the product was obtained as a white solid.

Workup

  1. temperaturewhile cooling with ice
  2. extractionwas then extracted with diethyl ether (4×100 ml)
  3. additionafter adding water (80 ml)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated by evaporation in vacuo
  6. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-bdf4c17dac6c4766852de17811b09022
Source dataset
uspto-grants-2009_10
Patent number
US07608619B2

Reaction notes

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