2-Bromoethanol → HCID 21960115, compound

HRID 1768565Notes

Reaction equation

HRID 1768565 reaction equation
Cl.[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.Br[CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH-:9].[NH4+:8].[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:11][CH2:12][N:13]([CH2:19][CH2:20][OH:21])[CH2:14][CH2:15]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 108982-Bromoethanol2×HCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochloride

Product 2

HCID 14923Ammonium HydroxideHCID 21960115HCID 21960115, compoundYield 166.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(6-Fluoro-1,2-benzisoxazol-3-yl)piperidine, hydrochloride (2.6 g, 10 mmol), 2-bromoethanol (1.3 ml, 15 mmol) and potassium carbonate (4.1 g, 30 mmol) in 25 ml dry acetone were refluxed for two hours and then stirred at 60° C. for 16 h, whereupon extra 0.4 ml (5 mmol) 2-bromoethanol was added. The mixture was then refluxed for 4 h, cooled to room temperature, concentrated in vacuo and taken up in water and methylene chloride. The organic phase was washed with water and saturated sodium chloride, dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (silica gel; methylene chloride:methanol:conc. ammonium hydroxide (80:20:0.5, v/v/v)) gave 2.2 g of 2-[4(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]ethanol. M.p. 119°-120° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was then refluxed for 4 h
  3. concentrationconcentrated in vacuo
  4. washThe organic phase was washed with water and saturated sodium chloride
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (silica gel

Sources & evidence

ORD record
ord-a727eeb881ab42008aa25706a6de03bd
Source dataset
uspto-grants-1995_01
Patent number
US05378714

Reaction notes

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