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

HRID 1821642Notes

Reaction equation

HRID 1821642 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([CH2:23]C[Mg]Cl)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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])[CH2:5][CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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 178418865HCID 178418865, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the aminonitrile 12 (21.93 g, 97 mmole) in absolute THF (180 ml) was added dropwise to a 1M solution of phenylethyl magnesium chloride in THF (242 ml, 242 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, 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. customdried
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e559fd2f74b6457aa76415ee8e257098
Source dataset
uspto-grants-2009_10
Patent number
US07608619B2

Reaction notes

Loading…