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

HRID 1030507노트

반응식

HRID 1030507 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 22179027Isopropanol ethanol용매

반응 조건

온도
125 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-7e7df78769fc4c87ba470923c231a5d9
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106857

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