Diisopropylethylamine → 6-Chloro-4-[[1-(3-phenylprop-2-enyl)piperidin-4-yl]amino]chromen-2-one

HRID 897195Notes

Reaction equation

HRID 897195 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[Cl:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[O:33][C:32](=[O:37])[CH:31]=[C:30]2OS(C(F)(F)F)(=O)=O>C(Cl)(Cl)Cl>[Cl:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[O:33][C:32](=[O:37])[CH:31]=[C:30]2[NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]=[CH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20817849HCID 20817849, compoundHCID 544281014-Amino-1-cinnamylpiperidine

Product 1

HCID 730020776-Chloro-4-[[1-(3-phenylprop-2-enyl)piperidin-4-yl]amino]chromen-2-oneYield 42.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-(3-Phenyl-allyl)-piperidin-4-ylamine (4) (1.01 g,4.65 mmol) and diisopropylethylamine (1.63 mL, 9.3 mmol) in 10 mL CHCl3 was added a solution of compound 3 (1.1 g, 5.6 mmol) in 10 mL CHCl3. The reaction was stirred at room temperature for about 3 hours. The reaction mixture was then washed with water and brine and dried with MgSO4. The yellow residue was triturated with a small volume of dichloromethane and filtered. The final product was converted to the HCl salt by addition of 4.0N HCl in dioxane to a suspension of the compound in dichloromethane. The solvent was removed by evaporation and the residue triturated with methanol to give the title compound (780 mg, 39%). 1H NMR (300 MHz, MeOD-d4) δ 1.92-2.22 (2H, m), 2.35-2.45 (2H, bd, J=11.8 Hz), 3.15-3.35 (2H, m), 3.65-3.75 (2H, bd, j=12.3), 3.85-4.0 (1H, m), 3.90-4.00 (2H, d, J=6.9 Hz), 5.46 (1H, s), 6.32-6.43 (1H, p, J=7.7 Hz), 6.92-6.98 (1H, d, J=16.2 Hz), 7.31-7.41 (4H, m), 7.52-7.54 (2H, m), 7.58-7.62 (1H, dd, J=2.0, 8.8 Hz), 8.148 (1H, s).

Workup

  1. washThe reaction mixture was then washed with water and brine
  2. dry with materialdried with MgSO4
  3. customThe yellow residue was triturated with a small volume of dichloromethane
  4. filtrationfiltered
  5. additionThe final product was converted to the HCl salt by addition of 4.0N HCl in dioxane to a suspension of the compound in dichloromethane
  6. customThe solvent was removed by evaporation
  7. customthe residue triturated with methanol

Sources & evidence

ORD record
ord-5752fbb4e3db4631951bea3b42a0e36b
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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