Hexamethylenetetramine → 1-(4-Pivaloylbenzyl)-3,5,7-triaza-1-azonia-adamantane bromide

HRID 2083119Notes

Reaction equation

HRID 2083119 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:5][CH:4]=1.[CH2:15]1[N:20]2[CH2:21][N:22]3[CH2:24][N:18]([CH2:19]2)[CH2:17][N:16]1[CH2:23]3>C(Cl)(Cl)Cl>[Br-:1].[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N+:16]23[CH2:17][N:18]4[CH2:24][N:22]([CH2:21][N:20]([CH2:19]4)[CH2:15]2)[CH2:23]3)=[CH:4][CH:5]=1)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 4101HexamethylenetetramineHCID 128310071-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

Product 1

HCID 203593951-(4-Pivaloylbenzyl)-3,5,7-triaza-1-azonia-adamantane bromide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

An ice solution of 127.5 g. (0.5 mole) of α-bromo-4-pivaloyl toluene in 600 ml. of chloroform is added dropwise to 77.0 g. (0.55 mole) of hexamethylene tetramine in 550 ml. chloroform. The resulting mixture is stirred for 2 days at room temperature and the solvent evaporated in vacuo. The residue is treated with ether and the resulting solid filtered and washed thoroughly with ether to give a white solid, 1-(4-pivaloylbenzyl)-3,5,7-triaza-1-azonia-adamantane bromide. The resulting solid is suspended in 300 ml. of 6N hydrochloric acid and steam distilled until no more formaldehyde is evolved. The distillation residue is poured onto ice and 180 ml. of 50% sodium hydroxide. The basic solution is extracted with ether and the ether is washed with water, brine and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is dissolved in ethanol and treated with ether/hydrochloric acid to give 4-pivaloyl benzylamine hydrochloride, m.p. 222° C. to 225° C.

Workup

  1. customthe solvent evaporated in vacuo
  2. additionThe residue is treated with ether
  3. filtrationthe resulting solid filtered
  4. washwashed thoroughly with ether

Sources & evidence

ORD record
ord-2da234ea287d49da8970e966270113b3
Source dataset
uspto-grants-1978_04
Patent number
US04084003

Reaction notes

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