Sodium borohydride → 4-Acetylaminomethyl-1-ethyl-1,2,3,6-tetrahydropyridine

HRID 973995Notes

Reaction equation

HRID 973995 reaction equation
[BH4-].[Na+].[I-].[C:4]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N+:12]([CH2:15][CH3:16])=[CH:11][CH:10]=1)(=[O:6])[CH3:5]>CO>[C:4]([NH:7][CH2:8][C:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH3:16])[CH2:11][CH:10]=1)(=[O:6])[CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 197755294-Acetylaminomethyl-1-ethylpyridinium iodide

Product 1

HCID 150234574-Acetylaminomethyl-1-ethyl-1,2,3,6-tetrahydropyridineYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

Sodium borohydride (21.96 g) was added portionwise to a solution of 4-acetylaminomethyl-1-ethylpyridinium iodide (44.43 g) in methanol (400 ml) below 20° C. and the mixture was stirred at 75° C. for 3 hours. The mixture was evaporated in vacuo and the residue was poured into 0.7N aqueous solution of sodium hydroxide (115 ml). The mixture was extracted with methylene chloride. The extracts were washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by vacuum distillation to give 4-acetylaminomethyl-1-ethyl-1,2,3,6-tetrahydropyridine (23.38 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionthe residue was poured into 0.7N aqueous solution of sodium hydroxide (115 ml)
  3. extractionThe mixture was extracted with methylene chloride
  4. washThe extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-7cedd8e75b1b44009c1c9af09a299115
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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