N,N-Dimethyltetradecylamine → 1-Adamantylcarbonylmethyldimethyltetradecylammonium bromide

HRID 1112628Notes

Reaction equation

HRID 1112628 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°.______________________________________ Found Calculated______________________________________Carbon 67.72 67.45Hydrogen 10.65 10.51______________________________________

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-7e7778b3d5d54b7fb5363a3104589223
Source dataset
uspto-grants-1978_10
Patent number
US04123513

Reaction notes

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