Acetonitrile → HCID 12050748, compound

HRID 1485207Notes

Reaction equation

HRID 1485207 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.C(#N)C.C(N(C(C)C)CC)(C)C>CCOC(C)=O.Cl>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 9590p-FluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 12050748HCID 12050748, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

tert-Butyl piperidin-4-ylcarbamate (1.200 g, 5.992 mmol) and 4-fluoronitrobenzene (0.705 g, 4.99 mmol) were placed in a 30 mL microwave vial then acetonitrile (20 mL) followed by diisopropylethylamine (1.778 mL, 9.986 mmol) were added. The reaction was heated under microwave irradiation at 150° C. for 15 minutes. The reaction mixture was diluted with EtOAc (200 mL) and 2 M aq. HCl (150 mL), the layers were separated and the aqueous layer was extracted with EtOAc (2×100 mL), the organics were combined and washed with brine (150 mL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound (I74) (1.040 g, 65%) as a yellow solid; 1H NMR (400 MHz, d6-DMSO) 8.06-7.99 (m, 2H), 7.03-6.97 (m, 2H), 6.88 (d, J=7.5 Hz, 1H), 4.01-3.93 (m, 2H), 3.62-3.47 (m, 1H), 3.13-3.02 (m, 2H), 1.85-1.74 (m, 2H), 1.44-1.30 (m, 11H).

Workup

  1. additionwere added
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  4. washwashed with brine (150 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d34dd823161469994cefd995fbfc7ba
Source dataset
uspto-grants-2016_08
Patent number
US09421205B2

Reaction notes

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