Acetaldehyde → 1-Benzyl-4-[N-ethyl-N-(3-ethylamino-2-pyridinyl)amino]methylpiperidine

HRID 361847Notes

Reaction equation

HRID 361847 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:23][CH3:24])[C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25](=O)[CH3:26].C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:23][CH3:24])[C:16]2[C:21]([NH:22][CH2:25][CH3:26])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 177Acetaldehyde2×HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 54076407HCID 54076407, compound

Product 1

HCID 543163461-Benzyl-4-[N-ethyl-N-(3-ethylamino-2-pyridinyl)amino]methylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-4-[N-ethyl-N-(3-amino-2-pyridinyl)amino]methylpiperidine (EXAMPLE 177, 2.35 g, 7.27 mmol) is dissolved in 18 ml methanol and cooled to 0°. Acetaldehyde (0.45 ml, 8.0 mmol) and sodium cyanoborohydride (685 mg, 10.9 mmol) is added. The mixture is stirred at 0° for one hr, then warmed to 20°-25°. Acetaldehyde and sodium cyanoborohydride are added in the same amounts as above two more times, cooling to 0° before and warming to 20°-25° after each addition. The mixture is poured into 1N sodium hydroxide, extracted with chloroform, dried over sodium sulfate, filtered and concentrated. Flash column chromatography (silica gel, 100 g; methanol/chloroform (5/95)), gives the title compound, NMR (300 MHz, CD3OD) 7.58, 7.31, 6.98, 3.49, 3.18, 3.00, 2.87. 1.93, 1.70, 1.40, 1.15 and 1.01δ.

Workup

  1. temperaturecooled to 0°
  2. temperaturewarmed to 20°-25°
  3. temperaturecooling to 0° before and
  4. temperaturewarming to 20°-25°
  5. additionafter each addition
  6. extractionextracted with chloroform
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-617cf2b5f36e4ae7932d838c64e10eb7
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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