8-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile → HCID 12595611, compound

HRID 1349386Notes

Reaction equation

HRID 1349386 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1([C:13]#N)[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.[C:16]1([Mg]Cl)[CH:21]=[CH:20]C=[CH:18][CH:17]=1>O1CCCC1>[CH3:1][N:2]([CH3:15])[C:3]1([C:13]2[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=2)[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 12595611HCID 12595611, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50.0 g of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile were dissolved in 400 ml of analytical grade tetrahydrofuran; 216 ml of a commercially available two molar solution of phenylmagnesium chloride in tetrahydrofuran were added dropwise under a nitrogen atmosphere, while cooling with an ice bath, and stirring was carried out overnight at room temperature. For working up, 200 ml of ice-cold ammonium chloride solution (20 wt. %) were added with stirring, while cooling with an ice bath, and after 30 minutes the phases were separated. The aqueous phase was extracted twice using 250 ml of ether each time, and the extracts were combined with the organic phase, washed with 200 ml of water followed by 200 ml of saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 60.0 g of dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-amine were obtained.

Workup

  1. temperaturewhile cooling with an ice bath
  2. stirringwith stirring
  3. temperaturewhile cooling with an ice bath
  4. customafter 30 minutes the phases were separated
  5. extractionThe aqueous phase was extracted twice
  6. washwashed with 200 ml of water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-37caca92d7bf47e18a45419dd689e6e8
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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