Methane → Pirtenidine hydrochloride

HRID 1904645Notes

Reaction equation

HRID 1904645 reaction equation
[CH2:1]([NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:16]([Cl:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C>ClCCl>[ClH:24].[CH2:16]([N:13]1[CH:14]=[CH:15][C:10](=[N:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:11]=[CH:12]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 297MethaneHCID 81421-Chlorooctane2×HCID 3017535N-Octylpyridin-4(1H)-imine

Product 1

HCID 151111Pirtenidine hydrochlorideYield 187.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
180 °C

Procedure

A mixture of 4-octylaminopyridine (25 g., 0.121 mole) and octyl chloride (20.5 ml., 0.121 mole) was heated at 180° C. for 1 hr. More octyl chloride (0.5 ml.) was added and the mixture was again heated at 180° C. for 1 hr., then dissolved in dichloromethane. The dichloromethane solution was treated with charcoal, filtered, and stripped of solvent under vacuum. The solid residue was slurried in ether (1.5 kg.), collected by filtration, washed with ether (500 g.), isolated in a dry bag, and dried (50°-80° C., 0.1 mm.). The procedure was repeated using the same amounts of starting materials and the product were combined, affording N-(1-octyl-4(1H)-pyridinylidene)octanamine monohydrochloride (80.5 g., 93% yield, m.r. 120°-125° C.), which is the monohydrochloride salt of the compound of Formula I wherein R and R' are both octyl.

Workup

  1. temperaturethe mixture was again heated at 180° C. for 1 hr
  2. filtrationfiltered
  3. filtrationcollected by filtration
  4. washwashed with ether (500 g.)
  5. customisolated in a dry bag
  6. customdried (50°-80° C., 0.1 mm.)

Sources & evidence

ORD record
ord-557f9ca95a27483e806fc487a3b07a52
Source dataset
uspto-grants-1989_06
Patent number
US04839372

Reaction notes

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