Potassium Carbonate → Hydrochloric Acid

HRID 842635Notes

Reaction equation

HRID 842635 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([CH2:13][C@@H:14]([NH:30][CH3:31])[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.[CH3:32][C:33]1([C:39]([Cl:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl.O>[CH:7]1([CH2:13][C@@H:14]([N:30]([CH3:31])[C:39]([C:33]2([CH3:32])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:40])[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)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.[ClH:41]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 41892451-Methylcyclohexanecarbonyl chlorideHCID 12052823HCID 12052823, compound

Product 2

HCID 313Hydrochloric AcidHCID 12052814HCID 12052814, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.08 g of potassium carbonate (0.58 mmol) in 1 ml. of water 1o was added a solution of 0.18 g of {(1R)-1-cyclohexylmethyl-2-[4-(2-methoxyphenyl)-piperidin-1-yl]-ethyl}-methyl-amine (0.58 mmol) in 10 mL of dichloromethane. The resulting mixture was cooled to 0° C. and 0.093 g of 1-methyl -cyclohexanecarboxylic acid chloride (0.58 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, and 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 0.220 g (75%) of white solid; mp=169-171° C.; MS(+)ESI m/z=469 (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-1edb871eff2147bea4eadbe74e0a3ed5
Source dataset
uspto-grants-2002_04
Patent number
US06376494B1

Reaction notes

Loading…