Sch 37370 → HCID 22914781, compound

HRID 1377578Notes

Reaction equation

HRID 1377578 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][N:19]([C:22](=[O:24])[CH3:23])[CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:25]=1.ClC1C=C(C=CC=1)C(OO)=[O:31]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][N:19]([C:22](=[O:24])[CH3:23])[CH2:20][CH2:21]3)[C:10]3=[N+:11]([O-:31])[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:25]=1

Participants

4

Reactant 2

HCID 60680Sch 37370HCID 70297m-Chloroperbenzoic acid

Product 1

HCID 22914781HCID 22914781, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 711 mg (2.01 mmole) of 8-chloro-11-(1-acetyl-4-piperidylidene)-6,11-dihydro-5 H-benzo[5,6]cyclohepta[1,2-b]pyridine in 30 ml of dry CH2Cl2 at -10° C. and under a nitrogen atmosphere was added 246 mg (1.60 mmole) of m-chloroperoxybenzoic acid. After 95 min. the mixture was taken up in CH2Cl2 and washed once with 10% aqueous sodium bisulfite and once with 10% aqueous sodium hydroxide. It was dried over magnesium sulfate, filtered, and concentrated in vacuo. The product was purified via flash chromatography (MeOH in CH2Cl2) and recrystallized from ethyl acetateexanes to give 175 mg of the title compound as a hemi-ethyl acetate solid. (m.p. 90.5°-93° C.)

Workup

  1. washwashed once with 10% aqueous sodium bisulfite and once with 10% aqueous sodium hydroxide
  2. dry with materialIt was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified via flash chromatography (MeOH in CH2Cl2)
  6. customrecrystallized from ethyl acetateexanes

Sources & evidence

ORD record
ord-a2ccaac3f00d4e91adcc98290436e93c
Source dataset
uspto-grants-1997_09
Patent number
US05665726

Reaction notes

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