Potassium Carbonate → HCID 86625191, compound

HRID 419380Notes

Reaction equation

HRID 419380 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][C@@H:22]4[CH2:24][C@H:19]3[CH2:20][NH:21]4)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C([O-])([O-])=O.[K+].[K+].I[CH2:32][CH2:33][F:34]>CN(C=O)C>[F:34][CH2:33][CH2:32][N:21]1[CH2:20][C@@H:19]2[CH2:24][C@H:22]1[CH2:23][N:18]2[CH:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-2×HCID 66649710HCID 66649710, compound

Product 1

HCID 86625191HCID 86625191, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (1S,4S)-2-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-2,5-diazabicyclo-[2.2.1]heptane (0.40 g, 1.2 mmol) and K2CO3 (0.38 g, 2.8 mmol) in DMF (10 mL) was added 1-iodo-2-fluoroethane (0.26 g, 1.5 mmol), and the reaction was stirred overnight. More 1-iodo-2-fluoroethane (50 mg, 0.29 mmol) was added, and the solution stirred an additional 4 h. The solvent was removed under vacuum, and the residue was taken up in DCM. Silica was added, and the solvent removed under vacuum. Silica gel chromatography provided the title compound of step C as a yellow oil (230 mg, 0.61 mmol, 49% yield). 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=9.3 Hz, 1H), 6.38 (dd, J=9.3, 2.4 Hz, 1H), 6.27 (d, J=2.4 Hz, 1H), 4.58-4.39 (m, 2H), 3.91 (s, 3H), 3.82-3.73 (m, 2H), 3.51 (br s, 1H), 3.34 (br s, 1H), 3.08-2.98 (m, 2H), 2.96-2.53 (m, 7H), 1.96-1.65 (m, 4H), 1.59-1.46 (m, 2H).

Workup

  1. stirringthe solution stirred an additional 4 h
  2. customThe solvent was removed under vacuum
  3. additionSilica was added
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-046f08d3f7ac4f389662d0e83cf4ffd6
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…