Hydrochloric Acid → 8-(1-Pyrrolidinyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

HRID 1095480Notes

Reaction equation

HRID 1095480 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]1[O:16][C:9]2([CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[O:8][CH2:7]1.[C-:17]#[N:18].[K+].Cl>O.CO>[N:1]1([C:12]2([C:17]#[N:18])[CH2:13][CH2:14][C:9]3([O:16][CH2:6][CH2:7][O:8]3)[CH2:10][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 31268PyrrolidineHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 3609768-(1-Pyrrolidinyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrileYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Pyrrolidine (22.5 ml, 0.306 mol), cyclohexane-1,4-dione monoethylene ketal (10.0 g, 0.064 mol) and potassium cyanide (10.0 g, 0.15 mol) was added to a mixture of 4 N hydrochloric acid (17 ml) and methanol (10 ml), while cooling with ice. The mixture was stirred at room temperature for 74 h and then, after addition of water (80 ml), extracted with diethyl ether (4×70 ml). After concentration, the residue was taken up in methylene chloride (70 ml) and the mixture was dried with magnesium sulfate overnight. The organic phase was concentrated and 8-pyrrolidin-1-yl-1,4-dioxaspiro[4.5]decane-8-carbonitrile was obtained as a white solid with a melting point of 65-67° C. in a yield of 68% (10.2 g).

Workup

  1. temperaturewhile cooling with ice
  2. extractionextracted with diethyl ether (4×70 ml)
  3. concentrationAfter concentration
  4. dry with materialthe mixture was dried with magnesium sulfate overnight
  5. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-73f4e0bb688b4c48965ea8f580136229
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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