Water → HCID 66703534, compound

HRID 1645396Notes

Reaction equation

HRID 1645396 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 4 (22.43 g, 100 mmol) in absolute ether (100 ml) was added dropwise to a 1 M solution of 4-chlorophenylmagnesium bromide in ether (200 ml, 200 mmol) under argon and while cooling with ice, and the mixture was stirred at RT for 20 hours. The reaction mixture was worked up by adding saturated ammonium chloride solution (100 ml) and water (100 ml) while cooling with ice, and extracting the mixture with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried and concentrated.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. extractionextracting the mixture with diethyl ether (3×100 ml)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-097aefb2b52d4de3abf828b462e26187
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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