N,N-Dimethyltetradecylamine → 1-Adamantylcarbonylmethyldimethyltetradecylammonium bromide

HRID 1657621Notes

Reaction equation

HRID 1657621 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 bromide

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°C.

Workup

  1. additionA mixture of 1.3g
  2. washThe next day the solidified mixture was washed with ether
  3. customrecrystallized from ethyl acetate
  4. customto yield 2.1g

Sources & evidence

ORD record
ord-fef565b05ff04c03aa322624d2c05ec9
Source dataset
uspto-grants-1976_06
Patent number
US03961074

Reaction notes

Loading…