Hydrogen Bromide → HCID 23339022, compound

HRID 28130Notes

Reaction equation

HRID 28130 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13](C(OCC)=O)[CH2:12][CH2:11]1.[BrH:21].C(=O)=O>>[BrH:21].[BrH:21].[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 280Carbon DioxideHCID 23338990HCID 23338990, compound

Product 1

HCID 23339022HCID 23339022, compound

Procedure

A mixture of 10 parts of ethyl 4-[(2,6-dimethylphenyl)amino]-1-piperidinecarboxylate and 135 parts of hydrobromic acid solution 48% is stirred at a temperature between 80° and 110° C. until the evolution of gaseous carbon dioxide is ceased (about one hour). The red-coloured reaction mixture is evaporated in vacuo. The residue is taken up in 56 parts of methylbenzene and the latter is evaporated again. Then evaporation is repeated in a mixture of 24 parts of 2-propanone and 40 parts of methylbenzene. The resulting semi-solid residue is triturated in 80 parts of hot 2-propanone and on cooling, the solid product is precipitated. It is filtered off, washed successively with small amounts of absolute ethanol and 2-propanone and dried, yielding 13 parts of N-(2,6-dimethylphenyl)-4-piperidinamine dihydrobromide; mp. +300° C.

Workup

  1. custom(about one hour)
  2. customThe red-coloured reaction mixture is evaporated in vacuo
  3. customthe latter is evaporated again
  4. customThen evaporation
  5. additionis repeated in a mixture of 24 parts of 2-propanone and 40 parts of methylbenzene
  6. customThe resulting semi-solid residue is triturated in 80 parts of hot 2-propanone
  7. temperatureon cooling
  8. customthe solid product is precipitated
  9. filtrationIt is filtered off
  10. washwashed successively with small amounts of absolute ethanol and 2-propanone
  11. customdried

Sources & evidence

ORD record
ord-82bc5ba03d8042c1b36f32d201347ce4
Source dataset
uspto-grants-1980_09
Patent number
US04225606

Reaction notes

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