Methane → Pirtenidine hydrochloride

HRID 745244Notes

Reaction equation

HRID 745244 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 products 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-6a3ccb0a15e643ffa66a6af7b2bc4073
Source dataset
uspto-grants-1986_07
Patent number
US04598082

Reaction notes

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