HCID 86715988, compound → HCID 66575659, compound

HRID 1430331Notes

Reaction equation

HRID 1430331 reaction equation
[Cl-].[Cl:2][CH2:3][N+:4]([CH3:13])([CH3:12])[CH2:5][CH2:6][CH2:7][C:8]([O:10]C)=[O:9]>O>[Cl:2][CH2:3][N+:4]([CH3:13])([CH3:12])[CH2:5][CH2:6][CH2:7][C:8]([O-:10])=[O:9]

Participants

3

Reactant 1

HCID 86715988HCID 86715988, compound

Product 1

HCID 66575659HCID 66575659, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-(chloromethyl)-4-methoxy-N,N-dimethyl-4-oxobutan-1-aminium chloride (5) (2.39 g, 10.38 mmol) in water (10 ml) was passed through Amberlite® IRA-410 (OH) ion exchange resin column (100 ml) slowly (ca. 0.5 ml/min) eluting with water. To the eluate Dowex® 50WX8 ion exchange resin by small portions was added until the pH of the medium of the initial 9.5 was decreased up to 6.8-7.0 (pH control by a pH-meter). The reaction mixture was filtered, evaporated, and the residue was azeotropically dried successively with acetone, isopropanol, and acetonitrile followed by drying in vacuo over P2O5 to give 1.69 g (91%) of 4-[(chloromethyl)(dimethyl)ammonio]butanoate. M.p. 100.5-101° C.

Workup

  1. washeluting with water
  2. additionTo the eluate Dowex® 50WX8 ion exchange resin by small portions was added until the pH of the medium of the initial 9.5
  3. filtrationThe reaction mixture was filtered
  4. customevaporated
  5. dry with materialthe residue was azeotropically dried successively with acetone, isopropanol, and acetonitrile
  6. dry with materialby drying in vacuo over P2O5

Sources & evidence

ORD record
ord-ba38fa0b483c4ac08652c564ffcf2c0c
Source dataset
uspto-grants-2015_01
Patent number
US08940793B2

Reaction notes

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