Ethanol → HCID 23109916, compound

HRID 1820293Notes

Reaction equation

HRID 1820293 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH2:11][CH2:12][C:13]1([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([N:27]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)[C:28]([C:30]3[O:31][CH:32]=[CH:33][CH:34]=3)=[O:29])[CH2:23][CH2:22]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)C.[ClH:45].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:45].[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][N:3]1[CH2:11][CH2:12][C:13]1([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([N:27]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)[C:28]([C:30]3[O:31][CH:32]=[CH:33][CH:34]=3)=[O:29])[CH2:25][CH2:26]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 702EthanolHCID 11489769HCID 11489769, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 23109916HCID 23109916, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After dissolving N-[1-[2-[1-[2-(1-oxo-2-isoindolinyl)ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (167 mg, 0.30 mmol) in ethyl acetate:ethanol=1:1 (4 mL), a 4N hydrochloric acid/ethyl acetate solution (0.25 mL, 1.00 mmol) was added. The reaction mixture was stirred at room temperature for 5 minutes and then concentrated under reduced pressure. The obtained residue was dissolved in ethanol (10 mL) and the solution was concentrated under reduced pressure to about 0.5 mL, after which 2-propanol (10 mL) was added and the mixture was concentrated under reduced pressure to obtain the title compound as a light brown amorphous substance (124 mg, 0.21 mmol) (70% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in ethanol (10 mL)
  3. concentrationthe solution was concentrated under reduced pressure to about 0.5 mL
  4. additionafter which 2-propanol (10 mL) was added
  5. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eb9788ada12644a88f872c776780feb7
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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