1-Bromooctane → HCID 14198639, compound

HRID 1904644Notes

Reaction equation

HRID 1904644 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]([Br:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CCOCC>[BrH: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

4

Reactant 2

HCID 81401-BromooctaneHCID 3017535N-Octylpyridin-4(1H)-imine

Product 1

HCID 14198639HCID 14198639, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-octylaminopyridine (10 g., 0.048 mole) and octyl bromide (8 ml., 0.048 mole) was heated at 125° C. for 8 hr. on one day and for 4 more hr. on the next day. The resulting solid was slurried, first in ether, then in ether-tetrahydrofuran (2:1) and finally in tetrahydrofuran, collected by filtration, washed with ether on the filter, and dried (70° C., 0.1 mm.) affording N-(1-octyl-4(1H)-pyridinylidene)octanamine monohydrobromide (11.95 g., 83% yield, m.r. 108°-112° C.), which is the monohydrobromide salt of the compound of Formula I wherein both R and R' are octyl.

Workup

  1. filtrationin ether-tetrahydrofuran (2:1) and finally in tetrahydrofuran, collected by filtration
  2. washwashed with ether on the filter
  3. customdried (70° C., 0.1 mm.)

Sources & evidence

ORD record
ord-bce5a123b8344015b1b08e2a9a6dcbff
Source dataset
uspto-grants-1989_06
Patent number
US04839372

Reaction notes

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