Hydrochloric Acid → Bendamustine Hydrochloride

HRID 2206999Notes

Reaction equation

HRID 2206999 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
37.5 °C

Procedure

4-{5-[Bis-(2-chloroethyl)amino]-1-methyl-1H-benzimidazol-2-yl}-butyric acid isopropyl ester (3 g) is charged into a round bottom flask and 50% hydrochloric acid solution (21 mL) is slowly added. The mixture is heated to 35-40° C., maintained for about 90 minutes, and concentrated under vacuum at about 55-58° C., to give a viscous mass. Warm water (12 mL, 55-60° C.) is added and the mixture is stirred for about 1 hour. The obtained solid is collected by filtration, washed with water (3 mL), and dried under vacuum at 45-50° C. for 4 hours to give bendamustine hydrochloride. Yield: 2.2 g (75%).

Workup

  1. temperaturemaintained for about 90 minutes
  2. concentrationconcentrated under vacuum at about 55-58° C.
  3. customto give a viscous mass
  4. filtrationThe obtained solid is collected by filtration
  5. washwashed with water (3 mL)
  6. customdried under vacuum at 45-50° C. for 4 hours

Sources & evidence

ORD record
ord-ceb2dff3a02d4d5194edcde8436cc111
Source dataset
uspto-grants-2016_06
Patent number
US09376394B2

Reaction notes

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