Bromine → HCID 13247732, compound

HRID 543710Notes

Reaction equation

HRID 543710 reaction equation
[Br:1]Br.[BrH:3].[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([CH2:13][C:14]([O:16][CH:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=[O:15])=[N:5]1>C(O)(=O)C>[BrH:1].[Br:3][CH:13]([C:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[O:4][N:5]=1)[C:14]([O:16][CH:17]1[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]1)=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 13247708HCID 13247708, compound

Product 1

HCID 13247732HCID 13247732, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of bromine (1.12 g) in glacial acetic acid (2 ml) was added dropwise at 60° C. with stirring to a solution of 1-methyl-4-piperidyl 1,2-benzisoxazole-3-acetate hydrobromide (2.0 g) in glacial acetic acid (8 ml). The reaction mixture was stirred for 3 hours at 60° C. and then concentrated in vacuo to about a half volume. The residue was dissolved in acetone and thereto was added diethyl ether until it became turbid. After cooling, the resulting crystals were collected by filtration to give 1-methyl-4-piperidyl 2-bromo-2-(1,2-benzisoxazol-3-yl)acetate hydrobromide (1.9 g). An analytical sample was obtained by recrystallization from ethanol, m.p. 169°-171° C.

Workup

  1. concentrationconcentrated in vacuo to about a half volume
  2. dissolutionThe residue was dissolved in acetone
  3. additionwas added diethyl ether until it
  4. temperatureAfter cooling
  5. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-083d4c8224504a9fb51c6068e9ad7c1e
Source dataset
uspto-grants-1984_05
Patent number
US04447439

Reaction notes

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