Triethylamine → N-[4-(4-Oxo-piperidin-1-yl)-phenyl]-butyramide

HRID 1061416Notes

Reaction equation

HRID 1061416 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].Cl.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[O:21]=[C:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 222202401-(4-Amino-phenyl)-piperidin-4-one hydrochloride

Product 1

HCID 22220544N-[4-(4-Oxo-piperidin-1-yl)-phenyl]-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Butyryl chloride (0.3 lmL, 2.94 mmol) was added to a solution of N-[4-(4-oxo-piperidine-1-yl)-phenyl]amine (which was obtained in Example 224) (0.70 g, 2.77 mmol) and triethylamine (1.9 mL, 13.9 mmol) in anhydrous methylene chloride (10 mL). The reaction was stirred overnight. The reaction was quenched with water (50 mL) and washed with methylene chloride (3×20 mL). The organic extracts were combined, dried (sodium sulfate) and concentrated. The desired product was isolated using silica gel flash chromatography to give the title compound as a yellow solid (0.41 g); 1H NMR (300 MHz, CDCl3) δ 1.01 (t, 3H, J=7.38 Hz), 1.72 (m, 2H), 2.29 (t, 2H, J=7.62 Hz), 2.55 (t, 4H, J=6.03 Hz), 3.55 (t, 4H, J=5.97 Hz), 6.95 (d, 2H, J=7.91), 7.42 (d, 2H, J=8.97 Hz). MS (ES) m/z: 260.9 (MH+); HRMS found for C15H20N2O2: 260.1511. Anal. Calcd. for C, 69.20; H, 7.74, N, 10.76. Found: C, 69.03; H, 7.94; N, 10.59.

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. washwashed with methylene chloride (3×20 mL)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d4828279cf3c4aec9d925f108e35f513
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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