4-(Trifluoromethyl)phenyl isocyanate → HCID 25070138, compound

HRID 929513Notes

Reaction equation

HRID 929513 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1>C1COCC1>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:11])[NH:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 25070138HCID 25070138, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Trifluoromethyl)phenyl isocyanate (1.068 g, 5.71 mmol) and 4-amino-1-Boc-piperidine (1.0 g, 5 mmol) was dissolved in THF (100 mL) and stirred for 12 h. The reaction was quenched by addition of water. The organic layer was isolated and the aqueous layer was extracted with EtOAc for 4 times. The combined organic layer was concentrated under vacuo and was further purified by flash chromatography (EtOAc:Hex/1:1) yielding final product (1.7 g, 4.39 mmol, 88%). 1H NMR (d6-DMSO, 300 Mhz): ∂ 8.77 (s, 1H), 7.55 (s, 4H), 6.26 (d, J=10 Hz, 1H), 3.80 (d, J=Hz, 2H), 3.64 (m, 1H), 2.88 (br, 2H), 1.78 (d, J=5 Hz, 2H), 1.38 (s, 9H), 1.23 (m, 2H).

Workup

  1. customThe reaction was quenched by addition of water
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was extracted with EtOAc for 4 times
  4. concentrationThe combined organic layer was concentrated under vacuo
  5. customwas further purified by flash chromatography (EtOAc:Hex/1:1)

Sources & evidence

ORD record
ord-ba356d97dbf44b489a59cc885c7b468f
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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