Hydrochloric Acid → 3-(N-Methylpentylamino)propionic acid hydrochloride

HRID 1350596

Reaction equation

HRID 1350596 reaction equation
C[O:2][C:3](=[O:13])[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[ClH:14]>O>[ClH:14].[CH3:12][N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][CH2:4][C:3]([OH:13])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16726422Methyl 3-(methyl(pentyl)amino)propanoate

Product 1

HCID 167264233-(N-Methylpentylamino)propionic acid hydrochlorideYield 82.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
24 °C

Procedure

68.8 g (367.4 mmol) N-methyl-N-pentyl-β-alanine methyl ester was hydrolyzed by refluxing with 138 ml water. Then the water is partly distilled off and 83 ml (472.7 mmol) hydrochloric acid (19%) was added. Water was distilled off again and 230 ml methyl ethyl ketone was added to remove residual water by azeotropic distillation. The reaction mixture was then cooled to 24° C. The crystallized product was separated and washed with methyl ethyl ketone and subsequently dried in vacuo. 63.7 g (82.7%) N-methyl-N-pentyl-β-alanine hydrochloride were obtained.

Workup

  1. distillationThen the water is partly distilled off
  2. distillationWater was distilled off again
  3. addition230 ml methyl ethyl ketone was added
  4. customto remove residual water
  5. distillationby azeotropic distillation
  6. customThe crystallized product was separated
  7. washwashed with methyl ethyl ketone
  8. customsubsequently dried in vacuo

Sources & evidence

ORD record
ord-744adb86bb3e4a93923a6ff91260a4e5
Source dataset
uspto-grants-2007_05
Patent number
US07214818B2

Linked notes

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