Potassium Carbonate → HCID 57244914, compound

HRID 1602930Notes

Reaction equation

HRID 1602930 reaction equation
Cl.[C:2]1([C@H:8]2[C@@H:13]([O:14][CH2:15][C:16]3[C:24]4[O:23][CH:22]=[CH:21][C:20]=4[CH:19]=[C:18]([C:25]4[N:29]([CH3:30])[N:28]=[N:27][CH:26]=4)[CH:17]=3)[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:31][CH2:32][C:33]#[C:34][CH2:35]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:31][CH2:32][C:33]#[C:34][CH2:35][N:9]1[CH2:10][CH2:11][CH2:12][C@H:13]([O:14][CH2:15][C:16]2[C:24]3[O:23][CH:22]=[CH:21][C:20]=3[CH:19]=[C:18]([C:25]3[N:29]([CH3:30])[N:28]=[N:27][CH:26]=3)[CH:17]=2)[C@@H:8]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131821,4-Dichloro-2-butyneHCID 67596365HCID 67596365, compound

Product 1

HCID 57244914HCID 57244914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [2S,3S]-2-phenyl-3-[(5-(1-methyl-1H-[1,2,3]triazol-5-yl)benzofuran-7-yl)methyloxy]piperidine hydrochloride (230 mg) in N,N-dimethylformamiide (2 ml) was slowly added to a solution of 1,4-dichlorobut-2-yne (106 ml) and potassium carbonate (224 mg) in N,N-dimethylformamide (2.0 ml). The solution was stirred for 18 hours at room temperature and the solvent removed under reduced pressure. To the residue was added water (40 ml) and the product was extracted with ethyl acetate (3×10 ml). The combined organic fractions were washed with water, saturated brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was purified by MPLC (10% ethyl acetate/hexane) to give [2S,3S]-1-(4-chlorobut-2-yn-1-yl)-2-phenyl-3-[(5-(1-methyl-1H-[1,2,3]triazol-5-yl)benzofuran-7-yl)methyloxy]piperidine as a yellow oil (205 mg). 1H NMR (360 MHz,CDCl3) δ1.57 (2H, m), 2.22 (2H, m), 2.98 (1H, m), 3.27 (2H, d, J=3.0 Hz), 3.43 (1H, br s), 3.62 (1H, br s), 3.95 (3H, s), 4.13 (2H, s), 4.46 (1H, d, J=11.0 Hz), 4.82 (2H, d, J=11.0 Hz), 6.77 (1H, d, J=1.0 Hz), 6.87 (1H, s), 7.15 (3H, m), 7.38 (2H, m), 7.43 (1H, s), 7.62 (2H, br s); MS m/z (CI+) 475 (M+H+).

Workup

  1. customthe solvent removed under reduced pressure
  2. additionTo the residue was added water (40 ml)
  3. extractionthe product was extracted with ethyl acetate (3×10 ml)
  4. washThe combined organic fractions were washed with water, saturated brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified by MPLC (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-62b35b0c15d54691911f65b60a7346a8
Source dataset
uspto-grants-1999_11
Patent number
US05985896

Reaction notes

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