Benzene, 1-chloro-3-isocyanato- → N-(3-chlorophenyl)-4-(2-(trifluoromethyl)phenoxy)piperidine-1-carboxamide

HRID 606271Notes

Reaction equation

HRID 606271 reaction equation
Cl.[F:2][C:3]([F:18])([F:17])[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[Cl:19][C:20]1[CH:21]=[C:22]([N:26]=[C:27]=[O:28])[CH:23]=[CH:24][CH:25]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:19][C:20]1[CH:21]=[C:22]([NH:26][C:27]([N:10]2[CH2:11][CH2:12][CH:7]([O:6][C:5]3[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=3[C:3]([F:2])([F:17])[F:18])[CH2:8][CH2:9]2)=[O:28])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 81531DiisopropylethylamineHCID 171780044-(2-(Trifluoromethyl)phenoxy)piperidine hydrochloride

Product 1

HCID 11223281N-(3-chlorophenyl)-4-(2-(trifluoromethyl)phenoxy)piperidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(2-trifluoromethylphenoxy)piperidine hydrochloride (42 mg, 0.15 mmol), 3-chlorophenyl isocyanate (36 mg, 0.30 mmol), and N,N-diisopropylethylamine (78 μL, 0.45 mmol) was stirred in dichloromethane (2 mL) at room temperature for overnight. The reaction mixture was diluted with dichloromethane and the solution was washed successively with 1N HCl, and NaHCO3 (sat.)/brine. The organic fraction was dried over MgSO4, filtered, and concentrated. The compound was purified by radial silica gel chromatography (1:20 to 1:2 ethyl acetate:hexanes) to afford the product which was 98% pure by LCMS analysis (15.7 mg, 26%).

Workup

  1. washthe solution was washed successively with 1N HCl, and NaHCO3 (sat.)/brine
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe compound was purified by radial silica gel chromatography (1:20 to 1:2 ethyl acetate:hexanes)
  6. customto afford the product which

Sources & evidence

ORD record
ord-5945733f9abc4babaa5c79a78509b4b6
Source dataset
uspto-grants-2011_03
Patent number
US07915293B2

Reaction notes

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