Sodium Bicarbonate → HCID 135494161, compound

HRID 1736090Notes

Reaction equation

HRID 1736090 reaction equation
C[O:2][C:3]1[CH:26]=[CH:25][C:6]2[C:7]([CH2:10][CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:14][CH2:13]3)=[N:8][O:9][C:5]=2[CH:4]=1.C([O-])(O)=O.[Na+]>Br>[OH:2][C:3]1[CH:26]=[CH:25][C:6]2[C:7]([CH2:10][CH2:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:16][CH2:17]3)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 9798502HCID 9798502, compound

Product 1

HCID 135494161HCID 135494161, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-methoxy-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole (0.1.1 g, 0.288 mmol) in 48% aqueous HBr (10 mL) was heated at 110° C. for 16 hours. The mixture was made basic by addition of saturated NaHCO3 and extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatography (3→6% MeOH-CH2Cl2) gave the title compound (0.055 g, 57%) as a white solid. M.p.: 148°-149° C.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel flash chromatography (3→6% MeOH-CH2Cl2)

Sources & evidence

ORD record
ord-39c29313d10844eb819dd26c68f6c32f
Source dataset
uspto-grants-1996_07
Patent number
US05538984

Reaction notes

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