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

HRID 361857Notes

Reaction equation

HRID 361857 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)[CH3:25].C([BH3-])#N.[Na+].O>CO.C(OCC)(=O)C>[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][CH3:25])=[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

7

Reactant 4

HCID 177Acetaldehyde2×HCID 962WaterHCID 5003444Sodium cyanoborohydride2×HCID 106627641-Benzyl-4-[N-ethyl-N-(3-amino-2-pyridinyl)amino]piperidine

Product 1

HCID 104972481-Benzyl-4-[N-ethyl-N-(3-(ethylamino)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-4-[N-ethyl-N-(3-(amino)-2-pyridinyl)amino]piperidine (EXAMPLE 204 Part B, 1.0 g, 3.22 mmol) is dissolved in methanol (8 ml) and cooled to 0°. The acetaldehyde (0.20 ml, 3.54 mmol) and sodium cyanoborohydride (0.31 g, 3.54 mmol) are added and the reaction is slowly warmed to 20°-25° and stirred for 18 hr. Then a further sodium cyanoborohydride (2 eq.) and 1.6 eq. of acetaldehyde are added and the reaction is stirred a further 20 hr. Then it is diluted with ethyl acetate and poured into water, washed with saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash column chromatography (silica gel; methanol/methylene chloride (2.5/97.5)), gives the title compound, NMR (300 MHz, CDCl3) 7.65, 7.40-7.17, 6.83, 6.71, 4.63, 3.42, 3.10-3.00, 2.93, 2.81, 1.92, 1.72-1.51, 1.17 and 079δ.

Workup

  1. temperaturecooled to 0°
  2. temperaturethe reaction is slowly warmed to 20°-25°
  3. stirringthe reaction is stirred a further 20 hr
  4. washwashed with saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica gel; methanol/methylene chloride (2.5/97.5))

Sources & evidence

ORD record
ord-529350b64fd8410cb4c316698816c0f4
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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