Methanol → HCID 68509584, compound

HRID 1419579Notes

Reaction equation

HRID 1419579 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]1([NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.CO>CN(C)C1C=CN=CC=1.ClCCl>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([CH2:12][N:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:3])[CH3:2])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 6367Acetyl chlorideHCID 54356602HCID 54356602, compound

Product 1

HCID 68509584HCID 68509584, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.71 mL, 0.79 g, 10.0 mmol) was added dropwise to a stirred, cooled (0° C.) solution of N-phenyl-1-t-butoxycarbonylpiperidine-4-methylamine (2.42 g, 8.3 mmol), pyridine (1.01 mL, 0.99 g, 12.5 mmol) and 4-dimethylaminopyridine (204 mg, 1.7 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 1 h. Methanol (5 mL) was added and the solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate (saturated, 50 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic fractions were washed with aqueous citric acid (10%, 2×50 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (2.73 g, 99%), δH (250 MHz, CDCl3) 7.47-7.15 (5H, m), 4.06 (2H, br m), 3.62 (2H, br m), 2.64 (2H, br m), 1.85 (3H, s), 1.66 (3H, m), 1.44 (9H, s), and 1.20 (2H, m).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionAqueous sodium hydrogen carbonate (saturated, 50 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  4. washThe combined organic fractions were washed with aqueous citric acid (10%, 2×50 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-101eea2e04ea4a5e93a80dc9a6ddc159
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

Loading…