Sodium Chloride → 1,4-Dioxa-8-azaspiro(4.5)decane

HRID 1508356Notes

Reaction equation

HRID 1508356 reaction equation
[OH-].[Na+].Cl.[O:4]1[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[O:7][CH2:6][CH2:5]1.[Cl-].[Na+]>O>[O:4]1[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[O:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 162187951,4-Dioxa-8-azaspiro[4.5]decane--hydrogen chloride (1/1)

Product 1

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneYield 93.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 30 L reactor equipped with a mechanic stirrer, an addition funnel and a septum was charged sodium hydroxide (NaOH, 1.4 kg, 35 mol, 2.0 equiv) and water (7 L) and the resulting solution was treated with 1,4-dioxa-8-azaspiro[4.5]decane hydrochloride (3.13 kg, 17.43 mol) at ambient temperature. The resulting mixture was then stirred at ambient temperature for 30 minutes before being saturated with solid sodium chloride (1.3 kg) and extracted with 2-methyl-tetrahydrofuran (3×7 L). The combined organic phase was dried with anhydrous sodium sulfate (Na2SO4, 1.3 kg) and concentrated under reduced pressure (70 mmHg) at 50° C. after removal of the drying reagent, sodium sulfate (Na2SO4), by filtration. The yellow oil thus obtained was distilled under reduced pressure (80 mmHg, by 115 to 120° C.) to afford 1,4-dioxa-8-azaspiro[4.5]decane (2.34 kg, 2.496 kg theoretical, 93.8%) as a clear oil, which was used directly in the subsequent coupling reaction.

Workup

  1. customTo a 30 L reactor equipped with a mechanic stirrer, an addition funnel
  2. extractionextracted with 2-methyl-tetrahydrofuran (3×7 L)
  3. dry with materialThe combined organic phase was dried with anhydrous sodium sulfate (Na2SO4, 1.3 kg)
  4. concentrationconcentrated under reduced pressure (70 mmHg) at 50° C.
  5. customafter removal of the drying reagent, sodium sulfate (Na2SO4)
  6. filtrationby filtration
  7. customThe yellow oil thus obtained
  8. distillationwas distilled under reduced pressure (80 mmHg, by 115 to 120° C.)

Sources & evidence

ORD record
ord-0d124a7bb7c94b7ca2d0ff33af45ef20
Source dataset
uspto-grants-2015_12
Patent number
US09221845B2

Reaction notes

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