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

HRID 1367606Notes

Reaction equation

HRID 1367606 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-679275a99c31458b974253cac2bf7915
Source dataset
uspto-grants-2011_02
Patent number
US07893258B2

Reaction notes

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