Water → (4-Chlorophenyl)-(1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine

HRID 12643

Reaction equation

HRID 12643 reaction equation
[CH3:1][N:2]([CH:4]([CH:7]1CCC2(OCCO2)C[CH2:8]1)[C:5]#N)[CH3:3].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1.[Cl-].[NH4+].[OH2:28].[CH3:29][CH2:30][O:31][CH2:32][CH3:33]>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:1][N:2]([CH:4]2[CH2:7][CH2:8][C:30]3([O:28][CH2:33][CH2:32][O:31]3)[CH2:29][CH2:5]2)[CH3:3])=[CH:20][CH:19]=1

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178478191HCID 178478191, compound

Product 1

HCID 79120490(4-Chlorophenyl)-(1,4-dioxa-spiro[4.5]dec-8-yl]-dimethylamine

Procedure

A solution of the aminonitrile 6 (22.43 g, 100 mmole) in absolute ether (100 ml) was added to a 1M solution of 4-chlorophenyl magnesium bromide in ether (200 ml, 200 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-b624ee5bc34e462b952ecc7a6393457b
Source dataset
uspto-grants-2010_06
Patent number
US07728028B2

Linked notes

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