N,N-Dimethyltetradecylamine → 1-Adamantylcarbonylmethyldimethyltetradecylammonium bromide

HRID 1112634Notes

Reaction equation

HRID 1112634 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 1.3 g. (0.005 mole) 1-adamantyl bromomethyl ketone and 1.23 g. (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 2.1 g white crystals, m.p. 134°-135.5°.

Workup

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

Sources & evidence

ORD record
ord-b5b23f48203b4e58a60c7b1385c22df8
Source dataset
uspto-grants-1978_10
Patent number
US04123515

Reaction notes

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