Tetrahydrofuran → [1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-3-phenylpropyl]-dimethylamine

HRID 557518Notes

Reaction equation

HRID 557518 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].C1COCC1.[C:22]1([CH2:28]C[Mg]Cl)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>C(OCC)C.O>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[CH2:5][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178418865HCID 178418865, compound

Product 1

HCID 66703150[1-(1,4-Dioxa-spiro[4.5]dec-8-yl)-3-phenylpropyl]-dimethylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of the aminonitrile 3 (21.93 g, 97 mmol) in abs. THF (180 ml) was added dropwise, under argon and while cooling with ice, to a 1M solution of phenylethylmagnesium chloride in THF (242 ml, 242 mmol), 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 and concentrated.

Workup

  1. additionwere added
  2. washThe organic phase was washed with water and saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1eae7dbd66fc422990741a0648103492
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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