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

HRID 557512Notes

Reaction equation

HRID 557512 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 mol), 1,4-dioxa-spiro[4.5]decane-8-carbaldehyde 2 (240 g, 0.141 mol) and potassium cyanide (22.05 g, 0.338 mol) were added, while cooling with ice, to a mixture of 4N hydrochloric acid (37 ml) and methanol (22 ml). The mixture was stirred for 4 d at room temperature and then, after addition of water (80 ml), extracted with diethyl ether (4×100 ml). The organic phase was dried over sodium sulfate and concentrated in vacuo, and the product was obtained in the form of 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 in vacuo
  4. customthe product was obtained in the form of a white solid

Sources & evidence

ORD record
ord-a348109e4acb49f68e13e71a6cc0b4ca
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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