N,N-Dimethyltetradecylamine → 1-Adamantylcarbonylmethyldimethyltetradecylammonium bromide

HRID 1112630Notes

Reaction equation

HRID 1112630 reaction equation
[Br:1][CH2:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].[CH3:15][N:16]([CH3:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CC(C)=O>[Br-:1].[C:5]12([C:3]([CH2:2][N+:16]([CH3:15])([CH3:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:4])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2

Participants

4

Reactant 2

HCID 8211N,N-DimethyltetradecylamineHCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketone

Product 1

HCID 867335111-Adamantylcarbonylmethyldimethyltetradecylammonium bromideYield 84.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.3g. (0.005 mole) 1-adamantyl bromomethyl ketone and 1.23g (0.005 mole) dimethyltetradecylamine was solubilized by the addition of 30cc acetone. The next day the solidified mixture was washed with ether and recrystallized from ethyl acetate to yield 2.1g white crystals, m.p. 134°-135.5°.

Workup

  1. additionA mixture of 1.3g
  2. washThe next day the solidified mixture was washed with ether
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fcce5987f824454fb29cff49638c917b
Source dataset
uspto-grants-1978_10
Patent number
US04123514

Reaction notes

Loading…