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

HRID 1645395Notes

Reaction equation

HRID 1645395 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 4 (2.24 g, 10 mmol) in absolute THF (10 ml) was added dropwise to a 1 M solution of thiophen-2-yl-magnesium bromide in THF (20 ml, 20 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 (10 ml) and water (10 ml) while cooling with ice, and extracting the mixture with diethyl ether (3×10 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 (3×10 ml)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a5e357f575694939ade6db1ac2885aaa
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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