Cyclohexanone → 1-Oxa-4-azaspiro[4.5]decane-4-ethanol

HRID 419778Notes

Reaction equation

HRID 419778 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[O:4]1[C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[N:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 8113DiethanolamineHCID 11430Potassium Carbonate

Product 1

HCID 753801-Oxa-4-azaspiro[4.5]decane-4-ethanolYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 50 mL flask containing diethanolamine (9,7 mL, 100 mmol) was added cyclohexanone (10,4 mL, 100 mmol, 1 eq.) and potassium carbonate (pulverized and dried at 160° C., 13,8 g, 100 mmol, 1 eq.). The reaction was stirred at 80° C. for 12 h. The reaction was cooled to room temperature and diluted with dichloromethane before filtering off potassium carbonate. The crude mixture diluted in cyclohexane was washed with water at 0° C. Drying with sodium sulfate and evaporation afforded the title product (8,4 g, 45% yield). 1H NMR (CDCl3, 400 MHz) d?(ppm): 3,91 (t, J=6,7 Hz, 2H); 3,60 (m, 2H); 3,00 (t, J=6,7 Hz, 2H); 2,70 (t, J=5,3 Hz, 2H); 1,72-1,50 (m, 7H); 1,43-1,30 (m, 2H); 1,21-1,04 (m, 1H). 13C NMR (CDCl3, 129,9 MHz) d?(ppm): 94,9; 63,2; 59,2; 50,3; 49,0; 32,6 (2C); 25,6; 23,3 (2C).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationbefore filtering off potassium carbonate
  3. additionThe crude mixture diluted in cyclohexane
  4. washwas washed with water at 0° C
  5. dry with materialDrying with sodium sulfate and evaporation

Sources & evidence

ORD record
ord-22ca2ca2194b4c69897193d354ae9c8a
Source dataset
uspto-grants-2012_01
Patent number
US08093398B2

Reaction notes

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