Ammonium Chloride → [-(4-Chlorophenyl)-1,4-dioxaspiro[4.5]dec-8-yl]dimethylamine

HRID 351331Notes

Reaction equation

HRID 351331 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Cl)=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:24])[C:12]1(C#N)[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH2:13]1.[Cl-].[NH4+]>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:18]2[CH2:17][O:16][C:15]3([CH2:20][CH2:21][CH:12]([N:11]([CH3:24])[CH3:10])[CH2:13][CH2:14]3)[O:19]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 178478983HCID 178478983, compound

Product 1

HCID 69429048[-(4-Chlorophenyl)-1,4-dioxaspiro[4.5]dec-8-yl]dimethylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Starting with 38 ml 1.0 molar 4-chlorophenyl magnesium chloride solution in diethylether, 4.00 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile, dissolved in 60 ml diethylether, were added dropwise and stirred overnight at ambient temperature. To work up the mixture, 30 ml ammonium chloride solution (20% by weight) were added with ice cooling, the phases were separated, the ethereal phase was washed in succession with 30 ml water and saturated sodium chloride solution, dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. The crude [-(4-chlorophenyl)-1,4-dioxaspiro[4.5]dec-8-yl]dimethylamine (4.18 g) obtained was initially stirred for 24 hours with a mixture of 10 ml concentrated hydrochloric acid (32% by weight) and 6.0 ml water at ambient temperature without further purification and then heated for 3 hours to reflux. Subsequently, the reaction mixture was first washed three times with 50 ml diethylether in each case, then made basic by addition of concentrated ammonia solution (25% by weight) with ice cooling, extracted three times with 100 ml diethylether in each case, the combined diethylether extracts were dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. 3.84 g 4-(4-chlorophenyl)-4-dimethylaminocyclohexanone were obtained as a brown oil.

Workup

  1. additionwere added dropwise
  2. additionwere added with ice cooling
  3. customthe phases were separated
  4. washthe ethereal phase was washed in succession with 30 ml water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d0d9f41e74e84d778154c190bb8dc51a
Source dataset
uspto-grants-2007_02
Patent number
US07183436B2

Reaction notes

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