Toluene → HCID 13076432, compound

HRID 223572Notes

Reaction equation

HRID 223572 reaction equation
[F:1][C:2]1[C:7]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14](C)[CH2:13][CH2:12]3)=[N:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26].C1(C)C=CC=CC=1>O>[C:28]1([O:27][C:25]([N:14]2[CH2:13][CH2:12][CH:11]([C:8]3[C:7]4[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=4[O:10][N:9]=3)[CH2:16][CH2:15]2)=[O:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 13076414HCID 13076414, compound

Product 1

HCID 13076432HCID 13076432, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.74 g of 4-fluoro-3-(1-methyl-4-piperidyl)-1,2-benzisoxazole, 1.25 g of potassium carbonate, 1.40 g of phenyl chloroformate and 50.0 ml of toluene was stirred under reflux for 8.0 hrs. The mixture was poured into water and the toluene layer was separated, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield an oil. The oil was purified by passing through a silica gel column (20:1), using 1% methanol in dichloromethane as the eluent. The eluent was evaporated and the residue solidified when scratched to yield a solid. The solid was recrystallized from petroleum-ether (bp 30°-60°) to yield 1.6 g (64%) of product, mp 108°-110°.

Workup

  1. temperatureunder reflux for 8.0 hrs
  2. customthe toluene layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto yield an oil
  6. customThe oil was purified
  7. customThe eluent was evaporated
  8. customto yield a solid
  9. customThe solid was recrystallized from petroleum-ether (bp 30°-60°)

Sources & evidence

ORD record
ord-759d9ee4d7784eabaa217ba49219c4ef
Source dataset
uspto-grants-1982_10
Patent number
US04355037

Reaction notes

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