Diethyl Ether → HCID 21970301, compound

HRID 1872683Notes

Reaction equation

HRID 1872683 reaction equation
Cl.[Br:2][C:3]1[CH:17]=[C:16]([CH3:18])[C:6]([O:7][CH2:8][C@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([CH3:15])[CH2:10]2)=[C:5]([CH3:19])[CH:4]=1.CC[O:22]CC.[OH-].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[Br:2][C:3]1[CH:17]=[C:16]([CH3:18])[C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][N@@+:11]([O-:22])([CH3:15])[CH2:10]2)=[C:5]([CH3:19])[CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69343836HCID 69343836, compound

Product 1

HCID 21970301HCID 21970301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-3-(4-Bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine hydrochloride (338 mg, 0.97 mmol) was partitioned between ether and aqueous sodium hydroxide. The ether was dried and concentrated to give an oil which was dissolved in dichloromethane (10 mL). To this solution was added m-chloroperbenzoic acid (327 mg, 50-60%). After 30 minutes, the reaction mixture was diluted with dichloromethane, then washed once with 10% aqueous sodium thiosulfate and three times with aqueous sodium bicarbonate. After drying, the dichloromethane solution was concentrated and the residue recrystallized from ethyl acetate to give (S)-3-(4-bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine-N-oxide (90.1 mg), m.p. 210.0-211.0° C.

Workup

  1. dry with materialThe ether was dried
  2. concentrationconcentrated
  3. customto give an oil which
  4. washwashed once with 10% aqueous sodium thiosulfate and three times with aqueous sodium bicarbonate
  5. customAfter drying
  6. concentrationthe dichloromethane solution was concentrated
  7. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-68051ae0b7d8459eb761ae4d745766cd
Source dataset
uspto-grants-2000_08
Patent number
US06110937

Reaction notes

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