Potassium Carbonate → HCID 178471781, compound

HRID 505306Notes

Reaction equation

HRID 505306 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][NH:13][CH2:14][CH3:15])[CH2:8][CH2:7]1)[CH3:2].F[C:18]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:19]=1[CH:20]=[O:21].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH2:14]([N:13]([CH2:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH2:7][CH2:8]1)[C:18]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:19]=1[CH:20]=[O:21])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehydeHCID 178464368HCID 178464368, compound2×

Product 1

HCID 178471781HCID 178471781, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of ethyl{trans-4-[(ethylamino)methyl]cyclohexyl}acetate (Intermediate 7; 130 mg; 0.57 mmol), 2-fluoro-5-(trifluoromethyl)benzaldehyde (100 mg; 0.52 mmol) and potassium carbonate (215 mg; 1.56 mmol) in toluene (4 mL) was heated at reflux for 14 h. The reaction was washed with H2O and sat. KHSO4 (10 mL each) and the aqueous layers were re-extracted with toluene (10 mL). The combined organic layers were washed with brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo to afford ethyl [trans-4-({ethyl[2-formyl-4-(trifluoromethyl)phenyl]amino}methyl)cyclohexyl]acetate as a yellow oil. LCMS=400.2 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 14 h
  3. washThe reaction was washed with H2O and sat. KHSO4 (10 mL each)
  4. extractionthe aqueous layers were re-extracted with toluene (10 mL)
  5. washThe combined organic layers were washed with brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96d551f4764c4b4fb37fa656ce58e330
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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