Potassium Carbonate → HCID 11949850, compound

HRID 251461Notes

Reaction equation

HRID 251461 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:16][C:17](=O)[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH:29]3[CH3:33])=[CH:20][CH:19]=2)([CH2:14][OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)F)CC)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([N:16]=[C:17]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH:29]4[CH3:33])=[CH:22][CH:23]=3)[O:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluoride2×HCID 11950910HCID 11950910, compound

Product 1

HCID 11949850HCID 11949850, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of N-[1-benzyl-4-(hydroxymethyl)piperidin-4-yl]-4-[3-(2-methylpyrrolidin-1-yl)propoxy]benzamide ax62 (0.46 g, 0.98 mmol) in dichloromethane (10 ml) is cooled at 0° C. and diethylaminosulfur trifluoride (180 μl, 1.47 mmol) is added. After stirring at 20° C. for 1.5 hours, the reaction mixture is cooled to 0° C. and another portion of diethylaminosulfur trifluoride (40 μl, 0.33 mmol) is added. This is repeated once more with another portion of 20 μl. Potassium carbonate (0.203 g, 1.47 mmol) is then added to the mixture, which is stirred at room temperature for 30 minutes. The mixture is then washed with a saturated solution of sodium bicarbonate, and the aqueous layer is extracted again with dichloromethane. The combined organic extracts are dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.453 g of an orange oil, which is purified by chromatography over silicagel (dichloromethane/methanol/ammonia 94:5.4:0.6) to give 0.17 g of 8-benzyl-2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-3-oxa-1,8-diazaspiro[4.5]dec-1-ene 30.

Workup

  1. temperaturethe reaction mixture is cooled to 0° C.
  2. stirringis stirred at room temperature for 30 minutes
  3. washThe mixture is then washed with a saturated solution of sodium bicarbonate
  4. extractionthe aqueous layer is extracted again with dichloromethane
  5. dry with materialThe combined organic extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2605eff51268476db496edfb34287d7d
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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