Hydrogen Bromide → HCID 23452515, compound

HRID 1278052Notes

Reaction equation

HRID 1278052 reaction equation
C[O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])=[CH:5][CH:4]=1.Br.[OH-].[Na+]>C(O)(=O)C>[OH:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 23452548HCID 23452548, compound

Product 1

HCID 23452515HCID 23452515, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Boil 6.2 g of 2-(4-methoxybenzyl)-1-methylpyrrolidine under reflux for 24 hours in a mixture of 30 ml of acetic acid and 30 ml of 48% strength hydrobromic acid. Add a further 20 ml of acetic acid and 20 ml of hydrobromic acid to the refluxed mixture and continue boiling for a further 24 hours. Pour the mixture onto 400 ml of ice water before adjusting its pH to 10 with 6 N sodium hydroxide solution and then extracting it 4 times with, in each case, 50 ml of diethyl ether. Dry the combined ether extracts over sodium sulfate and distil off the solvent. Recrystallize the resulting residue from 25 ml of ethanol to obtain a yield (65% of theory) of the title compound (m.p. 161° to 162°).

Workup

  1. extractionextracting it 4 times with, in each case, 50 ml of diethyl ether
  2. dry with materialDry the combined ether
  3. customdistil off the solvent
  4. customRecrystallize the resulting residue from 25 ml of ethanol
  5. customto obtain

Sources & evidence

ORD record
ord-878b4e065f7b46918ceb8549ecdcfbf7
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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