Trimethylamine → (S)-2,3-Dihydroxy-N,N,N-trimethylpropan-1-aminium chloride

HRID 1194578Notes

Reaction equation

HRID 1194578 reaction equation
[CH3:1][N:2]([CH3:4])[CH3:3].[Cl:5][CH2:6][C@H:7]([OH:10])[CH2:8][OH:9]>>[Cl-:5].[OH:10][C@H:7]([CH2:8][OH:9])[CH2:6][N+:2]([CH3:4])([CH3:3])[CH3:1]

Participants

3

Reactant 2

HCID 1146TrimethylamineHCID 148793(2R)-3-Chloro-1,2-propanediol

Product 1

HCID 13668848(S)-2,3-Dihydroxy-N,N,N-trimethylpropan-1-aminium chloride

Procedure

There was added 30 ml of 30 w/v % aqueous solution of trimethylamine to 11.05 g of (R)-3-chloro-1,2-propanediol (optical purity: 100% e.e., chemical purity: 99%). After reacting for 2 hours at room temperature, the reaction mixture was concentrated. After dissolving the concentrate in 30 ml of thermal ethanol, the solution was stored over night in a refrigerator. Thus, 15.26 g of (S)-2,3-dihydroxypropyltrimethylammonium chloride was obtained.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionAfter dissolving the
  3. concentrationconcentrate in 30 ml of thermal ethanol
  4. waitthe solution was stored over night in a refrigerator

Sources & evidence

ORD record
ord-4e74ea0491ca439a81b5398a73c53f0d
Source dataset
uspto-grants-1989_03
Patent number
US04814506

Reaction notes

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