Water → [(1,4-Dioxa-spiro[4.5]dec-8-yl)-phenyl-methyl]-dimethyl-amine

HRID 557513Notes

Reaction equation

HRID 557513 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].[C:17]1([Mg]Cl)[CH:22]=[CH:21]C=[CH:19][CH:18]=1.[Cl-].[NH4+].O>C1COCC1.C(OCC)C>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[C:5]3[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 66703149[(1,4-Dioxa-spiro[4.5]dec-8-yl)-phenyl-methyl]-dimethyl-amine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the aminonitrile 3 (23.56 g, 105 mmol) in abs. THF (100 ml) was added dropwise, under argon and while cooling with ice, to a 25% solution of phenylmagnesium chloride (144 ml, 262.5 mmol) in THF, and stirring was carried out for 20 h at RT. For working up the reaction mixture, saturated ammonium chloride solution (100 ml) and water (100 ml) were added, while cooling with ice, and extraction with diethyl ether (3×100 ml) was carried out. The organic phase was washed with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated.

Workup

  1. additionwere added
  2. washThe organic phase was washed with water and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab380fba1536495fb4e186c372f525ab
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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