Hydrochloric Acid → Bendamustine Hydrochloride

HRID 2207001Notes

Reaction equation

HRID 2207001 reaction equation
C([O:4][C:5](=[O:26])[CH2:6][CH2:7][CH2:8][C:9]1[N:13]([CH3:14])[C:12]2[CH:15]=[CH:16][C:17]([N:19]([CH2:23][CH2:24][Cl:25])[CH2:20][CH2:21][Cl:22])=[CH:18][C:11]=2[N:10]=1)(C)C.[ClH:27]>O>[CH3:14][N:13]1[C:9]([CH2:8][CH2:7][CH2:6][C:5]([OH:26])=[O:4])=[N:10][C:11]2[CH:18]=[C:17]([N:19]([CH2:20][CH2:21][Cl:22])[CH2:23][CH2:24][Cl:25])[CH:16]=[CH:15][C:12]1=2.[ClH:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53258886BendaMustine IMpurity C

Product 1

HCID 77082Bendamustine Hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
42.5 °C

Procedure

4-{5-[Bis-(2-chloroethyl)amino]-1-methyl-1H-benzimidazol-2-yl}-butyric acid isopropyl ester (4 g), is added to a mixture of water (13.6 mL) and concentrated hydrochloric acid (5.4 mL) in a round bottom flask. The mixture is heated to 40-45° C., maintained for 8 hours. Cooled the reaction mass to 25-30° C., stirred for 90 minutes, filtered, washed with water (12 mL), and dried under vacuum of 500-600 mm of Hg at 29° C. for 3 hours to give bendamustine hydrochloride. Yield: 2.7 g (75%).

Workup

  1. temperaturemaintained for 8 hours
  2. temperatureCooled the reaction mass to 25-30° C.
  3. filtrationfiltered
  4. washwashed with water (12 mL)
  5. customdried under vacuum of 500-600 mm of Hg at 29° C. for 3 hours

Sources & evidence

ORD record
ord-51534eff413e4da4848447f782c627bd
Source dataset
uspto-grants-2016_06
Patent number
US09376394B2

Reaction notes

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