Water → HCID 66703534, compound

HRID 1821640Notes

Reaction equation

HRID 1821640 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].[Cl:17][C:18]1[CH:23]=[CH:22]C([Mg]Br)=[CH:20][CH:19]=1.[Cl-].[NH4+].O>CCOCC>[Cl:17][C:18]1[CH:23]=[CH:22][C:5]([CH:4]([N:2]([CH3:3])[CH3:1])[CH:7]2[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178478191HCID 178478191, compound

Product 1

HCID 66703534HCID 66703534, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the aminonitrile 12 (22.43 g, 100 mmole) in absolute ether (100 ml) was added dropwise to a 1M solution of 4-chlorophenyl magnesium bromide in ether (200 ml, 200 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, 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. customdried
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7eff81b9e5bd439784fc83d56d9d165e
Source dataset
uspto-grants-2009_10
Patent number
US07608619B2

Reaction notes

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