HCID 14547259, compound → HCID 14547258, compound

HRID 1651093Notes

Reaction equation

HRID 1651093 reaction equation
OC(C1C=CC=CC=1)C([NH:5][CH:6]([CH2:16][CH3:17])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O>Cl>[CH2:16]([C@@H:6]([NH2:5])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH3:17]

Participants

3

Reactant 1

HCID 14547259HCID 14547259, compound

Product 1

HCID 14547258HCID 14547258, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

As in Example 16, a solution of 195 g of [R-(R*,R*)]-alpha-hydroxy-N-[1-ethyl-4-(3-pyridinyl)butyl]benzeneacetamide in 1.1 L of 6N HCl was treated with 104 mL of conc. HCl and then was heated at reflux for 2 days. The crude amine, obtained by the normal work up, was distilled to give 109 g of (R)-alpha-ethyl-3-pyridinebutanamine, (bp 105° C./0.2 mm); [α]D25 -11.9° (c, 1.0, MeOH)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customThe crude amine, obtained by the normal work up
  4. distillationwas distilled

Sources & evidence

ORD record
ord-a63f2cb933b744fbafdccf7699118047
Source dataset
uspto-grants-1990_05
Patent number
US04927826

Reaction notes

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