Chlorotrimethylsilane → HCID 12595612, compound

HRID 1948584Notes

Reaction equation

HRID 1948584 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1([C:13]#N)[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.[C:16]1([Mg][Cl:23])[CH:21]=[CH:20]C=[CH:18][CH:17]=1.[Cl-].[NH4+].Cl[Si](C)(C)C>C1COCC1>[ClH:23].[CH3:1][N:2]([CH3:15])[C:3]1([C:13]2[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=2)[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 12595612HCID 12595612, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (21 g, 0.1 mole), dissolved in THF (210 ml), was added within 15 minutes while cooling with ice and under argon to a 1.82 M phenylmagnesium chloride solution in THF (109 ml, 0.198 mole) and the mixture was then stirred for 16 hours at room temperature. To work up the reaction mixture saturated ammonium chloride solution (150 ml) was added while cooling with ice and extracted with diethyl ether (3×100 ml). The organic phase was extracted by shaking with water (100 ml) and saturated NaCl solution (100 ml) and concentrated by evaporation. A yellow oil (25.2 g) remained. The crude product was dissolved in ethyl methyl ketone (280 ml) and ClSiMe3 (18.8 ml, 0.15 mole) was added while cooling with ice. After a reaction time of 6 hours dimethyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine hydrochloride was isolated as a white solid in a yield of 35% (10.5 g).

Workup

  1. additionwas added within 15 minutes
  2. additionwas added
  3. temperaturewhile cooling with ice
  4. extractionextracted with diethyl ether (3×100 ml)
  5. extractionThe organic phase was extracted
  6. stirringby shaking with water (100 ml) and saturated NaCl solution (100 ml)
  7. concentrationconcentrated by evaporation
  8. dissolutionThe crude product was dissolved in ethyl methyl ketone (280 ml)
  9. temperaturewhile cooling with ice

Sources & evidence

ORD record
ord-3428524d95964ceb858dfd7a79ab82d1
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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