Cyclohexanone → 3,3-dimethyl-1-oxa-4-azaspiro[4.5]decane

HRID 1263379Notes

Reaction equation

HRID 1263379 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:8][C:9]([CH3:13])([CH3:12])[CH2:10]O>C1(C)C=CC=CC=1>[CH3:10][C:9]1([CH3:13])[NH:8][C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:7][CH2:12]1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 2769673,3-dimethyl-1-oxa-4-azaspiro[4.5]decaneYield 81.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 45 g (460 mmol) of cyclohexanone in 300 mL of toluene is added 35.6 g (400 mmol) of 2-amino-2,2-dimethylethanol. The reaction mixture is then heated to reflux and the by-product water is collected by a Dean-Stark trap. After 16 hours of heating at reflux, the reaction mixture is allowed to cool to ambient temperature and is then concentrated under vacuum to give 55 g of a yellow liquid. The product, identified by mass spectroscopy (m/z=169) is obtained in an 81.4% yield. The structure is confirmed by 1Hnmr.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux
  3. customthe by-product water is collected by a Dean-Stark trap
  4. temperatureAfter 16 hours of heating
  5. temperatureat reflux
  6. concentrationis then concentrated under vacuum

Sources & evidence

ORD record
ord-ee09be3eb1c6461d97787fa65958466c
Source dataset
uspto-grants-2003_04
Patent number
US06540795B2

Reaction notes

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