Hydrochloric Acid → HCID 47089487, compound

HRID 1500267Notes

Reaction equation

HRID 1500267 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(N(CC)C(C)C)(C)C.Cl.[N:21]1([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][N:23]=[CH:22]1>C(#N)C>[N:21]1([CH:26]2[CH2:31][CH2:30][N:29]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N+:8]([O-:10])=[O:9])[CH2:28][CH2:27]2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 157899224-(1H-Imidazol-1-yl)piperidine

Product 1

HCID 47089487HCID 47089487, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-fluoro-2-nitro-benzene (0.32 mmol, 34 μL), N,N-diisopropylethylamine (1.6 mmol, 0.28 mL) and HCl salt of 4-Imidazol-1-yl-piperidine (0.53 mmol, 0.10 g) in ACN (2 mL) was irradiated using microwave for 10 minutes at a temperature of 180° C. The solution was then cooled to room temperature and concentrated in vacuo and the resulting residue was purified using column chromatography on silica gel to provide 4-Imidazol-1-yl-1-(2-nitro-phenyl)-piperidine (71 mg, 81% yield). To the solution of this nitro compound in EtOAc (15 mL) was added Pd on carbon (5% Pd, 55 mg). The resulting reaction mixture was stirred under a hydrogen atmosphere at room temperature for about 15 hours. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to provide compound 41A (54 mg, 86% yield). HPLC-MS RT=0.63 minutes, mass calculated formula C14H18N4 242.15, observed LCMS m/z 243.30 (M+H).

Workup

  1. customfor 10 minutes
  2. customat a temperature of 180° C
  3. concentrationconcentrated in vacuo
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-21f2f32338a44b38b0e90a7935f7c0a0
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

Loading…