Water → HCID 24963707, compound

HRID 1666368Notes

Reaction equation

HRID 1666368 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:4][CH2:3]1.C([N:28]([CH2:31]C)[CH2:29][CH3:30])C.[F:33][C:34]1C=C[C:37](N=C=O)=[CH:36][CH:35]=1.[OH2:43]>ClCCl>[F:21][C:19]([F:22])([F:20])[C:16]1[CH:17]=[CH:18][C:13]([O:12][C:11]2[CH:10]=[C:9]([CH:25]=[CH:24][CH:23]=2)[CH:8]=[C:5]2[CH2:6][CH2:7][N:2]([C:31]([NH:28][C:29]3[CH:30]=[CH:37][CH:36]=[CH:35][C:34]=3[F:33])=[O:43])[CH2:3][CH2:4]2)=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride

Product 1

HCID 24963707HCID 24963707, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride (0.150 g) and triethylamine (0.124 mL, 2.20 equiv) in dichloromethane (2 mL, 0.2 M) was added 4-fluorophenyl isocyanate (0.050 mL, 1.1 equiv). The reaction was stirred at room temperature for 18 h. Water was added and the mixture was extracted with dichloromethane (2×). The combined organic extracts was washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (0-10% ethyl acetate/dichloromethane) to give the title compound as a white solid (0.172 g, 90% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.47 (2H, t, J=6.0 Hz), 2.61 (2H, t, J=5.6 Hz), 3.52 (2H, t, J=6.0 Hz), 3.61 (2H, t, J=5.8 Hz), 6.41 (1H, s), 6.64 (1H, d, J=3.5 Hz), 6.94-7.05 (5H, m), 7.07-7.12 (2H, m), 7.39 (1H, t, J=7.8 Hz), 7.90 (1H, dd, J=8.8, 2.5 Hz), 8.10 (1H, td, J=8.2, 1.7 Hz), 8.44 (1H, dd, J=1.6, 0.8 Hz).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×)
  2. washThe combined organic extracts was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-6275934af35a498b8f45e8ff3b082a6c
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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