Trichloroacetyl isocyanate → HCID 9948903, compound

HRID 2210543Notes

Reaction equation

HRID 2210543 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC(Cl)(Cl)[C:23]([N:25]=C=O)=[O:24]>C1COCC1.N>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:16][CH2:17][N:18]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 15295460HCID 15295460, compound

Product 1

HCID 9948903HCID 9948903, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)piperidine (3.63 mmol, 1.00 g) in dry THF (40 mL) at 0° C. was added trichloroacetylisocyanate (4.72 mmol, 0.889 mg; 563 μL) dropwise over 5 minutes. The resulting solution was stirred at 0° C. for 1 hour and at room temperature for 30 minutes. The reaction was diluted with NH3 saturated CH3CN solution (40 mL) and stirred at room temperature over the weekend. The volatiles were removed in vacuo and the residue partitioned between EtOAc (100 mL) and water (100 mL). The aqueous phase was extracted with EtOAc (1×100 mL), the combined organics washed with water (1×100 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2 :EtOAc) to afford the title compound as a white solid, mp=149°-150° C. (0.800 g, 70%).

Workup

  1. stirringstirred at room temperature over the weekend
  2. customThe volatiles were removed in vacuo
  3. customthe residue partitioned between EtOAc (100 mL) and water (100 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (1×100 mL)
  5. washthe combined organics washed with water (1×100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (SiO2 :EtOAc)

Sources & evidence

ORD record
ord-637b7c1505d846f5b94cb2a41313454e
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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