Potassium Carbonate → HCID 58117574, compound

HRID 405918Notes

Reaction equation

HRID 405918 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.Cl[CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:25]([N:26]([CH2:29][CH3:30])[CH2:27][CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][CH2:8]2)=[CH:20][CH:21]=1)[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 58117863HCID 58117863, compound

Product 1

HCID 58117574HCID 58117574, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7.9 g tert-butyl 4-(4-hydroxyphenoxy)-piperidine-1-carboxylate (see WO2006/64218), 5.2 g (2-chloroethyl)-diethylamine hydrochloride and 16.6 g potassium carbonate are placed in 250 ml acetone. The reaction mixture is stirred at reflux temperature. After 4 hours the inorganic salts are suction filtered and the mixture is evaporated to dryness. The residue is combined with ethyl acetate. The organic phase is washed with a saturated NaHCO3 solution, dried and evaporated to dryness. 10.1 g of the product are obtained as an oil.

Workup

  1. temperatureat reflux temperature
  2. filtrationsuction filtered
  3. customthe mixture is evaporated to dryness
  4. washThe organic phase is washed with a saturated NaHCO3 solution
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e2a88a34391f40ab9cb80e3f6d5b9b2f
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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