Benzylamine → HCID 178420324, 화합물

HRID 45924

반응식

HRID 45924 반응식
[N:1]1[C:5]2[CH:6]=[CH:7][C:8](C=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>CO>[CH2:12]([NH:19][C:8]1[CH:7]=[CH:6][C:5]2[NH:1][CH:2]=[N:3][C:4]=2[CH:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 4311764Sodium borohydrideHCID 100120381H-1,3-benzodiazole-5-carbaldehyde

생성물 1

HCID 178420324HCID 178420324, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.) was dissolved in MeOH (10 ml). Benzylamine (0.109 ml; 1 mmol; 1 eq.) was added and the mixture was stirred overnight. NaBH4 (57 mg; 1.5 mmol; 1.5 eq.) was added and stirring was continued overnight. The reaction was quenched by addition of water and extracted with ethyl acetate (3×25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was purified by flashchromatography on silica using a CHCl3/MeOH gradient. Yield: 0.045 g (19%); MS m/z: 238.4 [M+H]+; 1H-NMR (400 MHz, DMSO d6): δ 3.65 (s, 2H); 3.74 (s, 2H); 7.10-7.20 (m, 2H); 7.25-7.32 (m, 4H); 7.40-7.55 (m, 2H); 8.11 (s, 1H); 12.28 (br s, 1H); HPLC (METHOD [A]): rt 4.98 min (95.0%)

후처리

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction was quenched by addition of water
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flashchromatography on silica using a CHCl3/MeOH gradient
  8. customrt 4.98 min (95.0%)

출처 및 근거

ORD 기록
ord-5a9d3054390a48db92c7d01281f191d3
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541596B2

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