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Ethanol → HCID 23109914, compound

HRID 1820291
Notes
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Reaction equation

HRID 1820291 reaction equation
[ClH:1].C(OCC)(=O)C.[N:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]([CH2:47][C:48]2[CH:53]=[CH:52][N:51]=[CH:50][CH:49]=2)[CH2:16][CH2:17][C:18]2([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH:29]([N:32]([C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)[C:33]([C:35]4[O:36][CH:37]=[CH:38][CH:39]=4)=[O:34])[CH2:28][CH2:27]3)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:10][CH:9]=1.C(O)C>C(OCC)(=O)C>[ClH:1].[ClH:1].[ClH:1].[ClH:1].[N:51]1[CH:52]=[CH:53][C:48]([CH2:47][N:15]([CH2:14][C:11]2[CH:10]=[CH:9][N:8]=[CH:13][CH:12]=2)[CH2:16][CH2:17][C:18]2([CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][CH:29]([N:32]([C:40]4[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=4)[C:33]([C:35]4[O:36][CH:37]=[CH:38][CH:39]=4)=[O:34])[CH2:28][CH2:27]3)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:49][CH:50]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 11262076HCID 11262076, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 23109914HCID 23109914, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

After adding a 4N hydrochloric acid/ethyl acetate solution (0.35 mL, 1.4 mmol) to a solution of N-[1-[2-[1-[2-[bis(pyridin-4-ylmethyl)amino]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (171 mg, 0.28 mmol) in ethyl acetate (2 mL)-ethanol (2 mL), the mixture was stirred at room temperature for 10 minutes. Ethyl acetate (3 mL) was added to the reaction mixture, and after stirring for 20 minutes in an ice bath, the precipitated crystals were filtered out and dried under reduced pressure to obtain the title compound as a white solid (136 mg, 0.18 mmol) (64% yield).

Workup

  1. stirringafter stirring for 20 minutes in an ice bath
  2. filtrationthe precipitated crystals were filtered out
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-3f77e5b0528a4d36b40e86f525cf5b78
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601843B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes