3-Bromocyclohexene → HCID 54357020, compound

HRID 1977292Notes

Reaction equation

HRID 1977292 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:2].Br[CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]=[CH:21]1>O1CCCC1.[Ag]=O>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([O:17][CH:25]3[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 1370573-BromocyclohexeneHCID 12717445Ethyl 4-(4-hydroxypiperidin-1-yl)benzoate

Product 1

HCID 54357020HCID 54357020, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-hydroxypiperidin-1-yl)benzoic acid ethyl ester (5.4 g), silver oxide (5.31 g) and 3-bromocyclohexene (3.24 ml) in tetrahydrofuran (52 ml) was stirred for 1 day at room temperature. The reaction mixture was filtered off, and the filtrate was concentrated by evaporation under reduced pressure. To the residue was added ethyl acetate, and the resulting precipitate was collected by filtration and dried. The residue was purified by silica gel chromatography (3:2 hexane-ethyl acetate elution) to give 4-[4-(2-cyclohexenyloxy)piperidin-1-yl]benzoic acid ethyl ester (3.84 g).

Workup

  1. filtrationThe reaction mixture was filtered off
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. filtrationthe resulting precipitate was collected by filtration
  5. customdried
  6. customThe residue was purified by silica gel chromatography (3:2 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-d5ffdc885b8449e195c0d3dd38f93a74
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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