HCID 86715990, compound → HCID 70673855, compound
Reaction equation
[Br-].[Cl:2][CH2:3][CH2:4][N+:5]([CH3:14])([CH3:13])[CH2:6][CH2:7][CH2:8][C:9]([O:11]C)=[O:10]>O>[Cl-:2].[C:9]([CH2:8][CH2:7][CH2:6][N+:5]([CH2:4][CH2:3][Cl:2])([CH3:14])[CH3:13])([OH:11])=[O:10]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
N-(2-Chloroethyl)-4-methoxy-N,N-dimethyl-4-oxobutan-1-aminium bromide (5) (7.477 g, 25.9 mmol) was dissolved in water (10 ml) and passed through Amberlite® IRA-410 (Cl) ion exchange resin column (100 ml) slowly (ca. 0.5 ml/min) eluting with water (control with 2% AgNO3 solution). The eluate was evaporated; the residue (˜6 g) was dissolved in 1N HCl (50 ml) and stirred for 15 h at 70° C. The reaction mixture was evaporated and dried to give 4.755 g (79%) of 3-carboxy-N-(2-chloroethyl)-N,N-dimethylpropan-1-aminium chloride as a yellowish solid. The purity of the obtained compound can be increased by crystallization from acetonitrile. Thus, 2 g of the obtained material was crystallized from acetonitrile (120 ml) to afford 1.32 g of white crystalline 6 with m.p. 130° C.
Workup
- washeluting with water (control with 2% AgNO3 solution)
- customThe eluate was evaporated
- dissolutionthe residue (˜6 g) was dissolved in 1N HCl (50 ml)
- customThe reaction mixture was evaporated
- customdried
Sources & evidence
- ORD record
- ord-d7c9cf3338a440f5afb3ed6e3b3cda64
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940793B2
Reaction notes
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