Hydrogen Bromide → HCID 9866952, compound

HRID 1976271Notes

Reaction equation

HRID 1976271 reaction equation
[BrH:1].[CH3:2][N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.BrBr.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=1>C(O)(=O)C.C(OC)(C)(C)C>[BrH:1].[Br:1][CH:5]1[C:6]([C:15]2[C:16]([O:22][CH3:23])=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[O:13][CH3:12])=[CH:7][CH2:8][N:3]([CH3:2])[CH2:4]1

Participants

7

Reactant 4

HCID 260Hydrogen Bromide2×HCID 24408BromineHCID 693011,3,5-TrimethoxybenzeneHCID 740491-Methyl-4-piperidone

Product 1

HCID 9866952HCID 9866952, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

75.7 ml (0.44 mol) of 33% strength HBr in glacial acetic acid were added to 200 ml of glacial acetic acid, and 50 g (0.44 mol) of 1-methylpiperidin-4-one (III) were then rapidly added dropwise at 20-25° C. with ice-cooling. 70.4 g (0.44 mol) of bromine were added dropwise at 20-25° C. in the course of 30 min to the suspension of the hydrobromide obtained in this way, a clear, yellowish solution being obtained. This was stirred at 25° C. for a further 15 min and 67.2 g (0.40 mol) of 1,3,5-trimethoxybenzene (V) were then added to the reaction solution. It was then stirred at 25° C. for 1 h. After this, 300 ml of methyl tert-butyl ether were allowed to run in, the product being deposited in oily form. The supernatant was decanted off, the residue was stirred again with 300 ml of methyl tert-butyl ether and the supernatant was decanted off. The residue was then stirred with 150 ml of dichloromethane, the product crystallizing out. The 3(R,S)-bromo-1-methyl4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine hydrobromide (VI) obtained was filtered off with suction, washed with 50 ml of dichloromethane and dried in vacuo.

Workup

  1. additionwere then rapidly added dropwise at 20-25° C. with ice-
  2. temperaturecooling
  3. customobtained in this way
  4. customa clear, yellowish solution being obtained
  5. stirringIt was then stirred at 25° C. for 1 h
  6. customThe supernatant was decanted off
  7. stirringthe residue was stirred again with 300 ml of methyl tert-butyl ether
  8. customthe supernatant was decanted off
  9. stirringThe residue was then stirred with 150 ml of dichloromethane
  10. customthe product crystallizing out

Sources & evidence

ORD record
ord-97581d19394042969c87f79c16f7bdda
Source dataset
uspto-grants-2001_05
Patent number
US06225473B1

Reaction notes

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