Hydrogen Bromide → HCID 20343985, compound

HRID 2049880Notes

Reaction equation

HRID 2049880 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)#N.Cl.C(C1(C2C=CC=CC=2S[C:40]2[CH:45]=CC=CC=2)CCN(C)CC1)#N.S(Cl)(Cl)=[O:47].[BrH:50]>C(O)C>[BrH:50].[CH2:45]([C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1)=[O:47])[CH3:40]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 24386Thionyl ChlorideHCID 20343959HCID 20343959, compoundHCID 20343960HCID 20343960, compound

Product 1

HCID 20343985HCID 20343985, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-cyano-1-methyl-4-(2-phenylthiophenyl)-piperidine, free base of Example 3, in 15 ml of 48% hydrobromic acid is stirred at reflux for 16 hours. Thereafter, the excess acid is removed under reduced pressure, leaving a solid to which is added 10 ml of freshly distilled thionyl chloride. A clear solution results as the mixture is warmed on a steam bath. The excess thionyl chloride is distilled off, leaving a residue which is dissolved in 50 ml of absolute ethyl alcohol. The alcoholic solution is stirred at reflux for 1 hour and then permitted to stand for 16 hours. Then, the ethyl alcohol and any excess acid is removed under reduced pressure. The residue is dissolved in water and the aqueous solution is basified with dilute, ice cold sodium bicarbonate, liberating an amine which is dissolved in ether. The ethereal solution is dried before concentrating in vacuo. The residue, in ether, is converted to its hydrobromic acid salt which is recrystallized from a methyl alcohol-acetone-ether mixture to give 4-ethylcarbonyl-1-methyl-4-(2-phenylthiophenyl)piperidine hydrobromide.

Workup

  1. temperatureat reflux for 16 hours
  2. customThereafter, the excess acid is removed under reduced pressure
  3. customleaving a solid to which
  4. customA clear solution results as the mixture
  5. temperatureis warmed on a steam bath
  6. distillationThe excess thionyl chloride is distilled off
  7. customleaving a residue which
  8. temperatureat reflux for 1 hour
  9. customThen, the ethyl alcohol and any excess acid is removed under reduced pressure
  10. dissolutionThe residue is dissolved in water
  11. additionwith dilute
  12. dissolutionis dissolved in ether
  13. customThe ethereal solution is dried
  14. concentrationbefore concentrating in vacuo
  15. customis recrystallized from a methyl alcohol-acetone-ether mixture

Sources & evidence

ORD record
ord-e49241dc860f4e11ad912ac63dbf815e
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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