Hydrogen Bromide → HCID 19709982, compound

HRID 725892Notes

Reaction equation

HRID 725892 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[O:9][C:10]3[C:16]([O:17]C)=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH2:4][CH2:3]1.Br.[OH-].[Na+]>>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[O:9][C:10]3[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 19709989HCID 19709989, compound

Product 1

HCID 19709982HCID 19709982, compoundYield 36%

Conditions

Temperature
120 °C

Procedure

A mixture of 1-methyl-4-(7-methoxy-2-benzofuranyl)piperidine (5.6 g) and 48% HBr (40 mi) was stirred at 120° C. for 30 minutes. After cooling to room temperature, the mixture was neutralized with 10% sodium hydroxide solution and extracted with 1:1 ethyl acetate/1-butanol. The organic extract was washed with brine, concentrated and the resulting oil was chromatographed (silica gel, eluting with 20% MeOH/DCM and 0.5% NH4OH) to afford 1.9 g of 1-methyl-4-(7-hydroxy-2-benzofuranyl)piperidine.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with 1:1 ethyl acetate/1-butanol
  3. extractionThe organic extract
  4. washwas washed with brine
  5. concentrationconcentrated
  6. customthe resulting oil was chromatographed
  7. wash(silica gel, eluting with 20% MeOH/DCM and 0.5% NH4OH)

Sources & evidence

ORD record
ord-500ef90c4b81465e9d978e7cde786813
Source dataset
uspto-grants-1998_01
Patent number
US05708007

Reaction notes

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