Hydrochloric Acid → 4-Aminomethyl-1-ethyl-1,2,3,6-tetrahydropyridine

HRID 973996Notes

Reaction equation

HRID 973996 reaction equation
C([NH:4][CH2:5][C:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH:11]=1)(=O)C.[OH-].[Na+].Cl>CO>[NH2:4][CH2:5][C:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH3:13])[CH2:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 150234574-Acetylaminomethyl-1-ethyl-1,2,3,6-tetrahydropyridine

Product 1

HCID 150234584-Aminomethyl-1-ethyl-1,2,3,6-tetrahydropyridineYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-acetylaminomethyl-1-ethyl-1,2,3,6-tetrahydropyridine (20.0 g) and 6N aqueous solution of sodium hydroxide (73 ml) in methanol (150 ml) was refluxed for 40 hours. The solution was acidified with concentrated hydrochloric acid under ice cooling and evaporated in vacuo. To the residue was added ethanol (400 ml) and the mixture was refluxed for an hour. The resulting precipitates were filtered off and the filtrate was evaporated in vacuo. The residue was treated with Amberlite IRA-910 (trademark: Rohm & Haas Co.) and purified by vacuum distillation to give 4-aminomethyl-1-ethyl-1,2,3,6-tetrahydropyridine (14.25 g).

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added ethanol (400 ml)
  3. temperaturethe mixture was refluxed for an hour
  4. customThe resulting precipitates
  5. filtrationwere filtered off
  6. customthe filtrate was evaporated in vacuo
  7. additionThe residue was treated with Amberlite IRA-910 (trademark: Rohm & Haas Co.)
  8. distillationpurified by vacuum distillation

Sources & evidence

ORD record
ord-fe3df2e00a644707aa404ea53cedf97d
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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