alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide → (S)-2-Amino-5-(3-pyridyl)pentane

HRID 1110469Notes

Reaction equation

HRID 1110469 reaction equation
OC(C1C=CC=CC=1)C([NH:5][CH:6]([CH3:16])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O>Cl>[CH3:16][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

Participants

3

Reactant 1

HCID 13999762alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide

Product 1

HCID 13739742(S)-2-Amino-5-(3-pyridyl)pentane

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

As in Example 16, a solution of 16.3 g of [S-(S*,S*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide in 160 mL of 6N HCl was heated at reflux for 22 hours. The crude product, obtained by the usual work up was distilled to yield 8.3 g of (S)-alpha-methyl-3-pyridinebutanamine, (bp 85°-87° C./0.1 mm).

Workup

  1. temperatureat reflux for 22 hours
  2. customThe crude product, obtained by the usual work
  3. distillationup was distilled

Sources & evidence

ORD record
ord-b7b22e7a38bf43b6bd0432812b0c5f96
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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