Pyridine → HCID 21184178, compound

HRID 1872682Notes

Reaction equation

HRID 1872682 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 (3×), 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 (3×)
  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-899736121ef04929b04287a27eb49bf6
Source dataset
uspto-grants-2000_08
Patent number
US06110937

Reaction notes

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