Hydrogen Bromide → HCID 135856717, compound

HRID 1787532Notes

Reaction equation

HRID 1787532 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.[BrH:18]>>[BrH:18].[OH:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 10988161HCID 10988161, compound

Product 1

HCID 135856717HCID 135856717, compound

Procedure

Heat a stirred mixture of 6-methoxy-3-(1-piperazinyl)-1,2-benzisoxazole (0.1 mol), and 62% w/w hydrobromic acid (116.5 mL) at 115° C. under nitrogen for 6 hours. Partially concentrate under reduced pressure (15-20 mm Hg) at 50 to 60° C., add water (100 mL) and concentrate again. Repeat this process two times. Treat the residual heterogenous slurry with water (150 mL), age at 5° C. for 0.5 hour, and collect the solid by vacuum filtration. Wash the filter cake twice with cold water and dry to afford 6-hydroxy-3-(1-piperazinyl)-1,2-benzisoxazole hydrobromide (33.7 g). Suspend the crude material in water (830 mL), heat to 95-97° C., treat with activated charcoal (6.64 g), age at 95-97° C. for 0.25 hour, vacuum filter through celite, cool the filtrate to 5° C. and after 0.5 hour collect the product by vacuum filtration. Wash the filter cake twice with cold water and dry at 80° C. in high vacuum for 4 hours to afford 6-hydroxy-3-(1-piperazinyl)-1,2-benzisoxazole hydrobromide (23.5 g, 79%). The material was 99.8% pure by HPLC (Nucleosil C-18 column, 5 micron, 4.6×25 cm; mobile phase: NH4H2PO4 (0.05N):acetonitrile, 55:45 v/v; flow rate 1 mL/min; UV detection at 220/240 nm. MS (EI) 219 (M+)

Workup

  1. temperatureHeat
  2. concentrationPartially concentrate under reduced pressure (15-20 mm Hg) at 50 to 60° C.
  3. additionadd water (100 mL)
  4. concentrationconcentrate again
  5. additionTreat the residual heterogenous slurry with water (150 mL), age at 5° C. for 0.5 hour
  6. customcollect the solid
  7. filtrationby vacuum filtration
  8. washWash the filter cake twice with cold water
  9. customdry

Sources & evidence

ORD record
ord-656c2d6f1db34347af1ea43c2e6762ca
Source dataset
uspto-grants-2009_03
Patent number
US07511046B2

Reaction notes

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