Oxalic Acid → N-(1-Methyl-3-pyrrolidinyl)-1-(phenylmethyl)-1H-benzimidazol-2-amine

HRID 1030507Notes

Reaction equation

HRID 1030507 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH:3]=1.[CH2:8]([N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)C(O)=O>C(O)C.CC(O)C>[CH3:7][N:4]1[CH2:5][CH2:6][CH:2]([NH:1][C:16]2[N:15]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 38219871-Benzyl-2-chlorobenzimidazoleHCID 198206613-amino-N-methyl pyrroline

Product 1

HCID 9818015N-(1-Methyl-3-pyrrolidinyl)-1-(phenylmethyl)-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 22179027Isopropanol ethanolSolvent

Conditions

Temperature
125 °C

Procedure

To 14 g (0.14 mol) of 3-amino-N-methyl pyrroline was added 10.4 g (0.042 mol) of N-benzyl-2-chlorobenzimidazole and the reaction mixture heated to 125° C. for 2 days. The reaction mixture was partitioned between 150 mL of 1N NaOH and 100 mL of CH2Cl2. The aqueous layer was extracted again with 100 mL of CH2Cl2. The combined organic layers were washed with 100 mL of 1N NaOH, dried over Na2SO4, filtered, and concentrated by rotary evaporation and subjected to high vacuum at 100° C. for ~30 min. For purification, the residue was treated with 2 moles of oxalic acid in ethanol/2-propanol to afford 15 g (73%) of white analytically pure crystals, mp 211°-213° C. dec.

Workup

  1. customThe reaction mixture was partitioned between 150 mL of 1N NaOH and 100 mL of CH2Cl2
  2. extractionThe aqueous layer was extracted again with 100 mL of CH2Cl2
  3. washThe combined organic layers were washed with 100 mL of 1N NaOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. waitsubjected to high vacuum at 100° C. for ~30 min
  8. customFor purification
  9. customto afford 15 g (73%) of white analytically pure crystals, mp 211°-213° C. dec.

Sources & evidence

ORD record
ord-7e7df78769fc4c87ba470923c231a5d9
Source dataset
uspto-grants-1992_04
Patent number
US05106857

Reaction notes

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