Pyridine → HCID 21184178, compound

HRID 1384992Notes

Reaction equation

HRID 1384992 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:22]=[C:21]([CH3:23])[C:11]([O:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[CH2:15]3)=[C:10]([CH3:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>ClCCl.O.C(OCC)(=O)C>[C:31]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:22]=[C:21]([CH3:23])[C:11]([O:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][N:16]([CH3:20])[CH2:15]3)=[C:10]([CH3:24])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:33])[CH3:32]

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21184167HCID 21184167, compound

Product 1

HCID 21184178HCID 21184178, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[4-(3-aminophenyl)-2,6-dimethylphenoxymethyl]-1-methylpiperidine (513 mg, 1.58 mmol) in dichloromethane at 0° C. was added pyridine (1.3 mL, 16 mmol) and acetic anhydride (0.75 mL, 8.0 mmol). The mixture was stirred overnight at a temperature range from 0° C. to room temperature, and diluted with water and ethyl acetate. The aqueous layer was extracted with dichloromethane (3X), and the organic layers were dried and concentrated. The residue was purified on silica gel, eluting with 10% methanol/dichloromethane containing 0.5% ammonium hydroxide, to give 3-[4-(3-acetylaminophenyl)-2,6-dimethylphenoxymethyl]-1-methylpiperidine (479 mg, 82%).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (3X)
  2. customthe organic layers were dried
  3. concentrationconcentrated
  4. customThe residue was purified on silica gel
  5. washeluting with 10% methanol/dichloromethane containing 0.5% ammonium hydroxide

Sources & evidence

ORD record
ord-2f817a931846432da80d48adaa985289
Source dataset
uspto-grants-2001_07
Patent number
US06262078B1

Reaction notes

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