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

HRID 12642Notes

Reaction equation

HRID 12642 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].[F:17][C:18]1[CH:23]=[CH:22]C([Mg]Br)=[CH:20][CH:19]=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:22]=[CH:23][C:18]([F:17])=[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 178418676HCID 178418676, compound

Product 1

HCID 66703550[(1,4-Dioxa-spiro[4.5]dec-8-yl)-4-fluorophenylmethyl]-dimethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the aminonitrile 6 (19.89 g 88 mmole) in absolute THF (160 ml) was added dropwise under argon and cooling with ice to a 1M solution of 4-fluorophenyl magnesium bromide in THF (220 ml, 220 mmole) and stirred for 20 hours at RT. To work up the reaction mixture, saturated ammonium chloride solution (100 ml) and water (100 ml) were added while cooling with ice, and the mixture was extracted with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated by evaporation.

Workup

  1. additionwere added
  2. temperaturewhile cooling with ice
  3. extractionthe mixture was extracted 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 by evaporation

Sources & evidence

ORD record
ord-097883a3d0c64666940e3a5bdb9d6657
Source dataset
uspto-grants-2010_06
Patent number
US07728028B2

Reaction notes

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