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

HRID 12641Notes

Reaction equation

HRID 12641 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>O.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

7

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 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

40% aqueous dimethylamine solution (85 ml, 0.67 mole), 1,4-dioxa-spiro-[4.5]decane-8-carbaldehyde 5 (240 g, 0.141 mole) and potassium cyanide (22.05 g, 0.338 mole) were added while cooling with ice to a mixture of 4N hydrochloric acid (37 ml) and methanol (22 ml). The mixture was stirred for four days at room temperature and then, after adding water (80 ml), extracted with diethyl ether (4×100 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. extractionextracted with diethyl ether (4×100 ml)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated by evaporation in vacuo
  4. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-85f0a1c8da154ceeb53790dd29fb205d
Source dataset
uspto-grants-2010_06
Patent number
US07728028B2

Reaction notes

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