Propanal → 1-Benzyl-4-[N-ethyl-N-(3-propylamino-2-pyridinyl)amino]piperidine

HRID 361851Notes

Reaction equation

HRID 361851 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][CH3:23])[C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24](=O)[CH2:25][CH3:26].C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][CH3:23])[C:15]2[C:20]([NH:21][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=[CH:17][N:16]=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 527Propanal2×HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 106627641-Benzyl-4-[N-ethyl-N-(3-amino-2-pyridinyl)amino]piperidine

Product 1

HCID 675767231-Benzyl-4-[N-ethyl-N-(3-propylamino-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-4-[N-ethyl-N-(3-amino-2-pyridinyl)amino]piperidine (EXAMPLE 204B, 6.37 g, 20.56 mmol) and propionaldehyde (1.63 ml, 22.6 mmol) are dissolved in 50 ml methanol and cooled to 0°. Sodium cyanoborohydride (1.42 g, 22.6 mmol) is added and the mixture is warmed to 20°-25°. Twice more propionaldehyde (22.6 mmol) and sodium cyanoborohydride (22.6 mmol) are added, cooling the mixture to 0° before and warming to 20°-25° after each addition. The mixture is stirred 16 hr, then poured into 1N sodium hydroxide and extracted with dichloromethane. The extract is dried over sodium sulfate, filtered and concentrated. Chromatography (silica gel, 300 g; ethyl acetate/hexane (25/75)), gives the title compound, NMR (400 MHz, CDCl3) 7.72, 7.30, 6.91, 6.78, 4.79, 3.49, 3.14, 3.04, 2.87, 1.98, 1.73, 1.63, 1.01 and 0.86δ.

Workup

  1. temperaturecooled to 0°
  2. temperaturethe mixture is warmed to 20°-25°
  3. temperaturecooling the mixture to 0° before and
  4. temperaturewarming to 20°-25°
  5. additionafter each addition
  6. extractionextracted with dichloromethane
  7. dry with materialThe extract is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-70bef5f4582e480e9cc01fe77ef75a88
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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