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

HRID 1821638Notes

Reaction equation

HRID 1821638 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 12 (19.89 g, 88 mmole) in absolute THF (160 ml) was added dropwise to a 1M solution of 4-fluorophenyl magnesium bromide in THF (220 ml, 220 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 (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. temperaturewhile cooling with ice
  2. additionwere added
  3. temperaturewhile cooling with ice
  4. extractionthe mixture was extracted with diethyl ether (3×100 ml)
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1ef63cedd3f24e3e9ac48e095344ce46
Source dataset
uspto-grants-2009_10
Patent number
US07608619B2

Reaction notes

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