N,N-Dimethyltetradecylamine → 1-Adamantylcarbonylmethyldimethyltetradecylammonium bromide

HRID 1112632Notes

Reaction equation

HRID 1112632 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-a67b23b9dd7148ae8fcb3356e36c1f60
Source dataset
uspto-grants-1978_10
Patent number
US04123516

Reaction notes

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