Hexamethylenetetramine → 1-[2-(3,5-Dichloropyridin-2-yl)-2-oxoethyl]-1,3,5,7-tetraazatricyclo[3,3,1,13,7]decan-1-ium bromide

HRID 56008Notes

Reaction equation

HRID 56008 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][N:6]=1)=[O:4].[N:13]12[CH2:22][N:17]3[CH2:18][N:19]([CH2:21][N:15]([CH2:16]3)[CH2:14]1)[CH2:20]2>C(Cl)(Cl)Cl>[Br-:1].[Cl:11][C:10]1[C:5]([C:3](=[O:4])[CH2:2][N+:13]23[CH2:22][N:17]4[CH2:18][N:19]([CH2:21][N:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)=[N:6][CH:7]=[C:8]([Cl:12])[CH:9]=1

Participants

4

Reactant 2

HCID 4101HexamethylenetetramineHCID 534166072-Bromo-1-(3,5-dichloropyridin-2-yl)ethanone

Product 1

HCID 1180716121-[2-(3,5-Dichloropyridin-2-yl)-2-oxoethyl]-1,3,5,7-tetraazatricyclo[3,3,1,13,7]decan-1-ium bromideYield 97.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

5.00 g of the 2-bromo-1-(3,5-dichloropyridin-2-yl)ethanone prepared in Step 2 in Synthetic Example 2 in 30 ml of chloroform was added dropwise to 2.61 g of 1,3,5,7-tetraazatricyclo[3,3,1,13,7]decane in 50 ml of chloroform with stirring at room temperature, and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the precipitated crystals were collected by filtration and washed with 30 ml of chloroform to obtain 7.40 g of the desired product as white crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. customAfter completion of the reaction
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with 30 ml of chloroform

Sources & evidence

ORD record
ord-0e9acf13518646259019b6accebbd0fd
Source dataset
uspto-grants-2016_09
Patent number
US09434684B2

Reaction notes

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