Triethylamine → 4-Phenyl-2,8-diazaspiro[4.5]decan-1-one

HRID 914934Notes

Reaction equation

HRID 914934 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5](OCC)=O)[CH2:3][CH2:2]1.C([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])C.[C:19](OC(=O)OC(C)(C)C)(C)(C)[CH3:20].[O:31]1[CH2:36][CH2:35]OCC1.O>>[C:4]1([CH:10]2[C:35]3([CH2:16][CH2:15][NH:14][CH2:17][CH2:18]3)[C:36](=[O:31])[NH:1][CH2:11]2)[CH:3]=[CH:2][CH:20]=[CH:19][CH:5]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 127097244-Phenyl-2,8-diazaspiro[4.5]decan-1-oneYield 89%

Procedure

To a solution of ethyl isonipecotate (20 g, 127 mmol) in dioxane:water (1:1, 120 mlL) was added triethylamine (12.87 g, 127 mmol) at 0° C. followed by di-tert-butylcarbonate (35.2 g, 161 mmol) and the resulting mixture maintained at this temperature for 2 h. The product was then extracted with ethyl acetate (3×100 mL) and the combined organic extracts washed with HCl (1 N, 100 mL), brine (100 miL), dried over sodium sulfate, filtered and evaporated. Purification by Kugelrohr distillation afforded the title compound (29.0 g, 89%) as a colourless liquid, bp 140° C. at 0.13 mbar. MS: m/e=275.2 (M+NH4).

Workup

  1. temperaturethe resulting mixture maintained at this temperature for 2 h
  2. extractionThe product was then extracted with ethyl acetate (3×100 mL)
  3. washthe combined organic extracts washed with HCl (1 N, 100 mL), brine (100 miL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. distillationby Kugelrohr distillation

Sources & evidence

ORD record
ord-e44a1179f4324007b9bcbbfb43825b91
Source dataset
uspto-grants-2007_09
Patent number
US07265126B2

Reaction notes

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