Dichloromethane → Tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]1-piperidinecarboxylate

HRID 1832268Notes

Reaction equation

HRID 1832268 reaction equation
FC1[CH:3]=[C:4]([C@@H:9]2COC(=O)N2C(OC2C=CC([N+]([O-])=O)=CC=2)=O)[CH:5]=CC=1F.NCCC[N:31]1[CH2:36][CH2:35][CH:34]([C:37]2[CH:38]=[C:39]([NH:43][C:44](=[O:48])[CH:45]([CH3:47])[CH3:46])[CH:40]=[CH:41][CH:42]=2)[CH2:33][CH2:32]1.[C:49]([O-:52])([O-])=[O:50].[K+].[K+].[CH2:55](Cl)Cl>CO>[C:44]([NH:43][C:39]1[CH:40]=[CH:41][C:42]([CH3:55])=[C:37]([CH:34]2[CH2:33][CH2:32][N:31]([C:49]([O:52][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:50])[CH2:36][CH2:35]2)[CH:38]=1)(=[O:48])[CH:45]([CH3:46])[CH3:47]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 16757470N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}2-methylpropanamideHCID 600786674-nitrophenyl(4R)-4-(3,4-difluorophenyl)-2-oxo-1,3-oxazolidine-3-carboxylate

Product 1

HCID 16756289Tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]1-piperidinecarboxylateYield 10.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Nitrophenyl (4R)-4-(3,4-difluorophenyl)-2-oxo-1,3-oxazolidine-3-carboxylate (169 mg, 0.465 mmol), N-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-2-methylpropanamide (141 mg, 0.465 mmol), K2CO3 (0.193 g, 1.39 mmol), CH2Cl2 (10 mL), and methanol (0.1 mL) were combined in a flask. The mixture was stirred overnight at room temperature, the solvent was removed in vacuo, and the residue was purified by chromatography [2.5% of NH3 (2.0 M in methanol) in CH2Cl2] to afford the desired product (26.1 mg, 10.6%): 1H NMR (400 MHz, CDCl3) δ 8.08 (t, 1H, J=5.5 Hz), 7.45 (S, 2H), 7.38 (d, 1H, J=8.6 Hz), 7.24–7.12 (m, 3H), 7.06 (m, 1H), 6.97.(d, 1H, J=8.6 Hz), 5.40 (dd, 1H, J=3.9–8.8 Hz); 4.71 (t, 1H, J=8.8 Hz), 4.23 (dd, 1H, J=4.4, 9.1 Hz), 3.32 (qt, 2H, J=6.1 Hz), 2.99. (d, 2H, J=11.0 Hz), 2.49 (qt, 2H, J=7.0 Hz), 2.41 (t, 2H, J=7.0 Hz), 1.99–1.97 (m, 2H), 1.82–1.68 (m, 6H), 1.23 (d, 6H, J=7.3 Hz); Anal. Calcd. for C28H34F2N4O4+HCl+0.185CHCl3: C, 57.6; H, 6.04; N, 9.54. Found: C, 58.5; H, 6.08; N, 9.47; ESMS m/e: 529.1 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by chromatography [2.5% of NH3 (2.0 M in methanol) in CH2Cl2]

Sources & evidence

ORD record
ord-01076c29479946a1b20ae04728d755ea
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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