Tetrahydrofuran → [1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-3-phenylpropyl]-dimethylamine

HRID 1645394Notes

Reaction equation

HRID 1645394 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].C1COCC1.[C:22]1([CH2:28]C[Mg]Cl)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[CH2:5][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178418865HCID 178418865, compound

Product 1

HCID 66703150[1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-3-phenylpropyl]-dimethylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the aminonitrile 4 (21.93 g, 97 mmol) in absol. THF (180 ml) was added dropwise to a 1 M solution of phenylethylmagnesium chloride in THF (242 ml, 242 mmol) 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 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. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-76109a0776074cf6949bdbdc308426bf
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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