Water → [(1,4-Dioxa-spiro[4.5]dec-8-yl)-phenyl-methyl]-dimethyl-amine

HRID 1645393Notes

Reaction equation

HRID 1645393 reaction equation
[CH3:1][N:2]([CH:4]([CH:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1)[C:5]#N)[CH3:3].[C:17]1([Mg]Cl)[CH:22]=[CH:21]C=[CH:19][CH:18]=1.[Cl-].[NH4+].O>C1COCC1>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[C:5]3[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 66703149[(1,4-Dioxa-spiro[4.5]dec-8-yl)-phenyl-methyl]-dimethyl-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the aminonitrile 4 (23.56 g, 105 mmol) in absol. THF (100 ml) was added dropwise to a 25 percent strength solution of phenylmagnesium chloride (144 ml, 262.5 mmol) in THF under argon and while cooling with ice, and the mixture was stirred at RT for 20 hours. The reaction mixture was worked up by adding saturated ammonium chloride solution (100 ml) and water (100 ml) while cooling with ice, and extracting the mixture with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. extractionextracting the mixture with diethyl ether (3×100 ml)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d20f7c7cb55b4eefa3499c60a13e24cd
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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