18-Crown-6 → HCID 68551685, compound

HRID 1804858Notes

Reaction equation

HRID 1804858 reaction equation
C1(S(O[CH2:11][CH2:12][C:13]2([OH:29])[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([Cl:27])=[CH:21][C:20]=3[Cl:28])[CH2:15][CH2:14]2)(=O)=O)C=CC=CC=1.[Br-:30].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[Br:30][CH2:11][CH2:12][C:13]1([OH:29])[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([Cl:27])=[CH:21][C:20]=2[Cl:28])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 253877Potassium BromideHCID 86639803HCID 86639803, compound

Product 1

HCID 68551685HCID 68551685, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-(1-(2,4-dichloro-5-methoxyphenyl)-4-hydroxypiperidin-4-yl)ethyl benzenesulfonate (300 mg, 0.652 mmol) in acetone (5 mL) was treated with potassium bromide (194 mg, 1.629 mmol) and 18-crown-6 (189 mg, 0.717 mmol). The mixture was stirred at RT for 60 h before being concentrated in vacuo. The resultant residue was dissolved in EtOAc, and the resultant solution was washed with brine, dried (Na2SO4), and concentrated to give a residue. This residue was purified by a flash column using 0-30% EtOAc in heptanes as eluent to give 4-(2-bromoethyl)-1-(2,4-dichloro-5-methoxyphenyl)piperidin-4-ol (102 mg, 0.266 mmol, 41% yield) as a yellow oil.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in EtOAc
  3. washthe resultant solution was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a residue
  7. customThis residue was purified by a flash column

Sources & evidence

ORD record
ord-c31920485e024a7bb386dbc041e60446
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

Loading…