Pyridine → HCID 69411069, compound

HRID 1419589Notes

Reaction equation

HRID 1419589 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:27][NH2:28])[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.ClCCl.O.CO>[C:8]([O:12][C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:27][NH:28][C:1](=[O:3])[CH3:2])[CH2:19][CH2:20]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

9

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 4961274Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylate

Product 1

HCID 69411069HCID 69411069, compoundYield 58.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.40 mL, 0.43 g, 4.2 mmol) was added to a stirred, cooled (0° C.) solution of 2-(4-t-butoxycarbonylpiperazin-1-yl)phenylmethylamine (1.02 g, 3.5 mmol), 4-dimethylaminopyridine (86 mg, 0.7 mmol) and pyridine (0.57 mL, 0.55 g, 7 mmol) in dichloromethane (10 mL) and the mixture was stirred at room temperature for 1 h. Methanol (1 mL) was added and the mixture was stirred at room temperature for 2 h. Aqueous sodium hydrogen carbonate (saturated, 20 mL) and water (10 mL) were added and the mixture was extracted with dichloromethane (3×20 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by MPLC on silica gel, eluting with CH2Cl2 /MeOH/NH3 (Aq.) (99.5:0.5:0.05 increasing to 98:2:0.2) to give the title compound as a colorless solid (681 mg, 58%), δH (250 MHz, CDCl3) 7.28 (2H, m), 7.12 (2H, m), 6.26 (1H, br s), 4.55 (2H, d, J 5.6 Hz), 3.57 (4H, t, J 4.9 Hz), 2.86 (4H, t, J 4.9 Hz), 2.03 (3H, s), and 1.49 (9H, s). m/e (ES+) 334 (MH+).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. extractionthe mixture was extracted with dichloromethane (3×20 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by MPLC on silica gel
  6. washeluting with CH2Cl2 /MeOH/NH3 (Aq.) (99.5:0.5:0.05 increasing to 98:2:0.2)

Sources & evidence

ORD record
ord-22d4b725294c419bb97ad8532087e5eb
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

Loading…