Carbon Dioxide → 4-[4-(Trifluoromethoxy)phenoxy]piperidine

HRID 1039601Notes

Reaction equation

HRID 1039601 reaction equation
[OH-].[K+].C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)C.C(=O)=O>C(O)C(C)C>[F:25][C:22]([F:23])([F:24])[O:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 14797Potassium HydroxideHCID 68485568HCID 68485568, compound

Product 1

HCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidine

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent2×

Conditions

Temperature
100 °C

Procedure

Potassium hydroxide (10.7 g) was heated to 100° C., and dissolved in isobutanol (15 mL). An isobutanol (25 mL) solution of 1-ethoxycarbonyl-4-(4-trifluoromethoxyphenoxy)piperidine (12.03 g) was dropwise added thereto while noticing generation of carbon dioxide gas. After the dropwise addition, the mixture was heated and stirred at 100° C. for 2 hours; then the solvent was concentrated; and toluene (40 mL) was added to the obtained residue. The toluene solution was washed with water (40 mL×2), and then the solvent was concentrated under reduced pressure to obtain a target compound as a light orange solid substance. The yield amount was 5.73 g (98% based on trifluoromethoxyphenol).

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe mixture was heated
  3. concentrationthen the solvent was concentrated
  4. additionand toluene (40 mL) was added to the obtained residue
  5. washThe toluene solution was washed with water (40 mL×2)
  6. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-89ef3452cdf54d6d86e0b914fa936344
Source dataset
uspto-grants-2013_10
Patent number
US08552188B2

Reaction notes

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