Sodium Hydroxide → 7-(Pyridin-3-yl)heptan-1-amine

HRID 1583422Notes

Reaction equation

HRID 1583422 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14]C(=O)C)[CH:2]=1.[OH-].[Na+]>Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13557529N-[7-(Pyridin-3-yl)heptyl]acetamide

Product 1

HCID 135575307-(Pyridin-3-yl)heptan-1-amineYield 81.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 5.1 g of N-[7-(3-pyridyl)heptyl]acetamide was heated to reflux in diluted hydrochloric acid overnight. The mixture was cooled, made basic with 50% sodium hydroxide solution and was extracted with dichloromethane. The combined organic layers were dried over potassium carbonate and were evaporated. The residue was distilled to give 3.4 g of 3-pyridine heptanamine, bp 175°-180° C./0.4 mm.

Workup

  1. temperatureThe mixture was cooled
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over potassium carbonate
  4. customwere evaporated
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-3805197ade654298a29bb3b30b38035f
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

Loading…