Sodium Hydroxide → N,N,N-Trimethyl-3-(methylamino)propan-1-aminium bromide

HRID 263166Notes

Reaction equation

HRID 263166 reaction equation
[BrH:1].[Br-].[CH3:3][N+:4]([CH3:11])([CH3:10])[CH2:5][CH2:6][CH2:7][NH:8][CH3:9].[OH-].[Na+]>CO>[Br-:1].[CH3:3][N+:4]([CH3:11])([CH3:10])[CH2:5][CH2:6][CH2:7][NH:8][CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20320282N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide

Product 1

HCID 21444211N,N,N-Trimethyl-3-(methylamino)propan-1-aminium bromide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of 876.0 g. (3.0 moles) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide in 2.75 liters of absolute methanol at room temperature is added a freshly prepared solution of sodium hydroxide (120.0 g., 3.0 moles) in 1.0 liter of absolute methanol over a period of 1.0 hour. The reaction mixture is evaporated under reduced pressure and the solid residue is shaken with 750 ml. of acetonitrile. The insoluble sodium bromide is removed by filtration and the filtrate is evaporated. The solid residue is dried in vacuo to give a quantitative yield of white, crystalline hygroscopic product which may be used without further purification or can be recrystallized from isopropanol-ether. NMR (D2O)δ: 2.28 (3H, S, --NHCH3); 3.11 (9H, S, --N+ (CH3)3).

Workup

  1. additionTo a stirred suspension of 876.0 g
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customThe insoluble sodium bromide is removed by filtration
  4. customthe filtrate is evaporated
  5. customThe solid residue is dried in vacuo
  6. customto give a quantitative yield of white, crystalline hygroscopic product which
  7. custommay be used without further purification
  8. customcan be recrystallized from isopropanol-ether

Sources & evidence

ORD record
ord-0662e61bc0864b209a7ae4a35a23a5d4
Source dataset
uspto-grants-1979_05
Patent number
US04156693

Reaction notes

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