Potassium Carbonate → Hydrochloric Acid

HRID 842636Notes

Reaction equation

HRID 842636 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([CH2:13][C@@H:14]([NH2:30])[CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH2:18][CH2:17]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:31][C:32]([CH3:37])([CH3:36])[C:33]([Cl:35])=[O:34]>ClCCl.O>[CH:7]1([CH2:13][C@@H:14]([NH:30][C:33](=[O:34])[C:32]([CH3:37])([CH3:36])[CH3:31])[CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH2:20][CH2:21]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[ClH:35]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 62493Pivaloyl chlorideHCID 12052822HCID 12052822, compound

Product 2

HCID 313Hydrochloric AcidHCID 12052815HCID 12052815, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.076 g of potassium carbonate (0.54 mmol) in 1 ml. of water was added a solution of 0.18 g of {(1R)-1-cyclohexylmethyl-2-[4-(2-methoxyphenyl)-piperidin-1-yl]-ethyl}-amine (0.54 mmol) in 10 mL of dichloromethane. The resulting mixture was cooled to 0° C. and 0.066 g of trimethylacetyl chloride (0.54 mmol) was added. The reaction was allowed to stir overnight at 0° C., and was then diluted with 5 mL of water and 20 mL of dichloromethane and the phases separated. The aqueous phase was extracted with three additional portions of dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to yield the crude product, which was purified by flash chromatography on silica gel (dichloromethane/methanol) and converted to the hydrochloride.0.75 hydrate salt of the title compound with isopropanolic HCl to yield 0.137 g (56%) of white solid; mp=97-99° C.; MS(+)ESI m/z=415 (M+H)+.

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase was extracted with three additional portions of dichloromethane
  3. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customto yield the crude product, which
  7. customwas purified by flash chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-831fc701958640ed8f9da5b92ce1c2d6
Source dataset
uspto-grants-2002_04
Patent number
US06376494B1

Reaction notes

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