Water → N-Ethylpyridine-4-methylamine

HRID 874197Notes

Reaction equation

HRID 874197 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH2:9]([NH2:11])[CH3:10].[BH4-].[Na+].O>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:11][CH2:9][CH3:10])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6341EthylamineHCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 96681N-Ethylpyridine-4-methylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.70 g (0.147 mol) of 4-pyridine-formaldehyde was dissolved in 200 mL of ethanol, added under stirring in cold-water-bath with 21 g (0.296 mol) of 65-70% ethylamine aqueous solution, reacted for 0.5 h, monitored with TLC until the reaction was almost completed. Added carefully with 5.6 g (0.148 mol) of sodium borohydride in several batches, small amount in each batch, after the end of addition, added with 30 mL of water, reacted overnight (20 h), the reaction was completed according to TLC monitoring. Evaporated to remove solvent, added with water, extracted with dichloromethane, washed with water and saturated saline in order, dried with anhydrous sodium sulfate, evaporated to remove solvent to obtain yellow thick liquid, 30 g, crude yield 73.4%. 1H NMR(CDCl3, 400 MHz)δ: 1.14(t, 3H, J=7.00 Hz), 2.66(q, 2H, J=7.00 Hz), 3.81(s, 2H), 7.26-7.27(m, 2H), 8.52-8.54(m, 2H).

Workup

  1. additionadded
  2. customreacted for 0.5 h
  3. additionafter the end of addition
  4. customreacted overnight (20 h)
  5. customEvaporated
  6. customto remove solvent
  7. additionadded with water
  8. extractionextracted with dichloromethane
  9. washwashed with water and saturated saline in order
  10. dry with materialdried with anhydrous sodium sulfate
  11. customevaporated
  12. customto remove solvent
  13. customto obtain yellow thick liquid, 30 g, crude yield 73.4%

Sources & evidence

ORD record
ord-280a2856eaed4904b56db681a40302d7
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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