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

HRID 2073304Notes

Reaction equation

HRID 2073304 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 11062727(R)-2-Amino-5-(3-pyridyl)pentane

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A solution of 145 g of [R-(R*,R*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide in 900 mL of 6N HCl was treated with 80 mL of conc. HCl and then was heated at reflux for 2 days. After most of the solvent was removed under reduced pressure, the residue was made decidedly basic with 10N NaOH in an argon atmosphere and extracted with dichloromethane (1×1.2L; 2×600 mL). The dried (K2CO3) extracts were evaporated and the crude product was distilled to give 78.5 g of (R)-alpha-methyl-3-pyridinebutanamine, (bP 95° C./0.2 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customAfter most of the solvent was removed under reduced pressure
  4. extractionextracted with dichloromethane (1×1.2L; 2×600 mL)
  5. dry with materialThe dried (K2CO3) extracts
  6. customwere evaporated
  7. distillationthe crude product was distilled

Sources & evidence

ORD record
ord-d721bdcdd9744d7d9a4d6cb176eaccc5
Source dataset
uspto-grants-1990_04
Patent number
US04916145

Reaction notes

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