Triethylamine → HCID 22220427, compound

HRID 1061352Notes

Reaction equation

HRID 1061352 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:24]=1>C(Cl)Cl>[O:15]=[C:12]1[CH2:11][CH2:10][N:9]([C:6]2[CH:7]=[CH:8][C:3]([NH:2][S:29]([C:25]3[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=3)(=[O:31])=[O:30])=[CH:4][CH:5]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 3164136Pyridine-3-sulfonyl chlorideHCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochloride

Product 1

HCID 22220427HCID 22220427, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(4-amino-phenyl)-piperidine-4-one hydrochloride (which was obtained in Example 224) (8.76 g, 0.32 mol) in methylene chloride (100 mL) at room temperature was added triethylamine (9 mL). To this mixture was added a mixture of 3-pyridinesulfonyl chloride (7.45 g, 0.035 mol) and triethylamine (9 mL). The reaction was stirred for 18 hours. The reaction mixture was concentrated. The product was flash silica gel chromatographed eluting with 7:3 ethyl acetate/hexanes and then flash silica gel chromatographed eluting with 3% methanol in methylene chloride to give the titled compound as a yellow solid (1.34 g, 13%); 1H NMR (300 MHz, CDCl3) δ 2.54 (t, J=6 Hz, 4H), 3.56 (t, J=6 Hz, 4H), 6.79 (s, 1H), 6.85 (d, J=12 Hz, 2H), 6.98 (d, J=12 Hz, 2H), 7.40 (m, 1H), 7.97 (dd, J=3 Hz, 1H), 8.75 (dd, J=6 Hz, 1H), 8.90 (d, J=3 Hz, 1H); MS (ES) m/z: 331.9 (MH+, 100%); HRMS Calcd. for C16H17N3O3S(MH+): 332.1063. Found: 332.1063.

Workup

  1. additionTo this mixture was added
  2. concentrationThe reaction mixture was concentrated
  3. customchromatographed
  4. washeluting with 7:3 ethyl acetate/hexanes
  5. customflash silica gel chromatographed
  6. washeluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-a6258f22263e4c35992169df4a8ed000
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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