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

HRID 361822Notes

Reaction equation

HRID 361822 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][CH2:23][CH3:24])[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:25](=O)[CH3:26].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>C(O)C.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:22][CH2:23][CH3:24])[C:15]2[C:20]([NH:21][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

8

Reactant 5

HCID 177Acetaldehyde2×HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2×HCID 105680191-Benzyl-4-[N-propyl-N-(3-amino-2-pyridinyl)amino]piperidine

Product 1

HCID 540721561-Benzyl-4-[N-propyl-N-(3-ethylamino-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-4-[N-propyl-N-(3-amino-2-pyridinyl)amino]piperidine (EXAMPLE 114, 0.35 g) in absolute ethanol (4.3 ml) under nitrogen is treated with acetaldehyde (120 μl) and sodium cyanoborohydride (84 mg) and the pH is adjusted to 5 with glacial acetic acid as measured on moistened pH test paper. The resulting mixture is stirred at 20°-25° for 48 hrs, during which additional acetaldehyde (180 μl) and sodium cyanoborohydride (70 mg) is added, and is then adjusted to pH 3 with hydrochloric acid (3M), neutralized with sodium hydroxide (5%), and concentrated under reduced pressure. The residue is chromatographed (silica gel, 70-230 mesh, 35 g; eluting with a gradient of methanol/methylene chloride (1/99-2/98)) to give the title compound, NMR (CDCl3) 7.72, 7.31, 7.27, 6.91, 6.79, 4.66, 3.51, 3.10, 2.92, 2.05, 1.74, 1.27 and 0.79δ.

Workup

  1. additionis added
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is chromatographed (silica gel, 70-230 mesh, 35 g
  4. washeluting with a gradient of methanol/methylene chloride (1/99-2/98))

Sources & evidence

ORD record
ord-83d3acd38e8e44baa45448bb7c510357
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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