Hexamethylenetetramine → 1-(2-Oxo-2-phenylethyl)-1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decan-1-ium bromide

HRID 2367348Notes

Reaction equation

HRID 2367348 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH2:11]1[N:16]2[CH2:17][N:18]3[CH2:20][N:14]([CH2:15]2)[CH2:13][N:12]1[CH2:19]3>C(Cl)(Cl)Cl>[Br-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:12]12[CH2:13][N:14]3[CH2:20][N:18]([CH2:17][N:16]([CH2:15]3)[CH2:11]1)[CH2:19]2

Participants

4

Reactant 2

HCID 4101HexamethylenetetramineHCID 6259Phenacyl bromide

Product 1

HCID 137167301-(2-Oxo-2-phenylethyl)-1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decan-1-ium bromideYield 96.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

2-Bromo-1-phenylethanone (2.0 g, 10.05 mmol) was added to a solution of hexamethylenetetramine (1.409 g, 10.05 mmol) in CHCl3 (60 mL), and the resulting mixture was heated at 50° C. for 1 hour. The mixture was cooled to room temperature and the white precipitate was collected by filtration, washed with CHCl3, and dried under vacuo to afford the title compound (3.3 g) as a white solid. LC-MS (ES) m/z=259 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe white precipitate was collected by filtration
  3. washwashed with CHCl3
  4. customdried under vacuo

Sources & evidence

ORD record
ord-1fd3902c76ce4f5bbb8ae0d84c59d039
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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