Water → [(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiophen-2-yl-methyl]-dimethylamine

HRID 1821641Notes

Reaction equation

HRID 1821641 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].[S:17]1C=[CH:20][CH:19]=[C:18]1[Mg]Br.[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[S:17][CH:18]=[CH:19][CH:20]=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 178418438HCID 178418438, compound

Product 1

HCID 66703411[(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiophen-2-yl-methyl]-dimethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the aminonitrile 12 (2.24 g, 10 mmole) in absolute THF (10 ml) was added dropwise to a 1M solution of thiophen-2-yl-magnesium bromide in THF (20 ml, 20 mmole) under argon and while cooling with ice, and stirred for 20 hours at RT. To work up the reaction mixture saturated ammonium chloride solution (10 ml) and water (10 ml) were added while cooling with ice and the mixture was extracted with diethyl ether (3×10 ml). The organic phase was washed with water and saturated sodium chloride solution, dried and concentrated by evaporation.

Workup

  1. temperaturewhile cooling with ice
  2. additionwere added
  3. temperaturewhile cooling with ice
  4. extractionthe mixture was extracted with diethyl ether (3×10 ml)
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-91f7abb999ad49f8bbb9df874171631a
Source dataset
uspto-grants-2009_10
Patent number
US07608619B2

Reaction notes

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