Potassium Carbonate → HCID 22126486, compound

HRID 1858582Notes

Reaction equation

HRID 1858582 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C)[CH2:10][CH:9]2[O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:34]([O:36][CH2:37][C:38]([Cl:41])([Cl:40])[Cl:39])=[O:35]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:34]([O:36][CH2:37][C:38]([Cl:41])([Cl:40])[Cl:39])=[O:35])[CH2:10][CH:9]2[O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 22128384(3RS,4RS)-4-(4-chloro-phenyl)-1-methyl-3-(naphthalen-2-ylmethoxy)-piperidine

Product 1

HCID 22126486HCID 22126486, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.526 g (1.43 mmol) of (3RS,4RS)-4-(4-chloro-phenyl)-1-methyl-3-(naphthalen-2-ylmethoxy)-piperidine in 12 ml of toluene was treated with 100 mg of potassium carbonate and heated to 100°. Subsequently, 0.423 g (0.288 ml, 2 mmol) of 2,2,2-trichloroethyl chloroformate was added thereto and the mixture was stirred at 100° for 12 hours. The reaction solution was evaporated, taken up in 50 ml of ethyl acetate and washed with 20 ml of water and 20 ml of saturated sodium hydrogen carbonate solution. Drying over magnesium sulphate, filtration (sic) and evaporation yielded a colourless oil which was chromatographed on silica gel using a 3:2 mixture of hexane and ethyl acetate as the eluent. There was obtained 0.426 g (57% of theory) of 2,2,2-trichloroethyl 4-(4-chloro-phenyl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless oil; Rf : 0.31 (silica gel, hexane/ethyl acetate: 3/2).

Workup

  1. temperatureheated to 100°
  2. customThe reaction solution was evaporated
  3. washwashed with 20 ml of water and 20 ml of saturated sodium hydrogen carbonate solution
  4. dry with materialDrying over magnesium sulphate, filtration (sic) and evaporation
  5. customyielded a colourless oil which
  6. customwas chromatographed on silica gel using
  7. additiona 3:2 mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-05dc704af286487a9fea048e81fc012b
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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