Hydrochloric Acid → Benzenemethanamine, 3,5-difluoro-4-methoxy-alpha-methyl-

HRID 911318노트

반응식

HRID 911318 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:11](=O)[CH3:12])[CH:5]=[C:6]([F:10])[C:7]=1[O:8][CH3:9].C([O-])(=O)C.[NH4+].C([BH3-])#[N:20].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:11]([NH2:20])[CH3:12])[CH:5]=[C:6]([F:10])[C:7]=1[O:8][CH3:9]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 27369833',5'-Difluoro-4'-methoxyacetophenoneHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 55273519Benzenemethanamine, 3,5-difluoro-4-methoxy-alpha-methyl-수율 40.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Slurry 3′,5′-difluoro-4′-methoxyacetophenone (1.0 g, 5.0 mmol), ammonium acetate (4.14 g, 50 mmol) and sodium cyanoborohydride (630 mg, 20 mmol) in anhydrous methanol (35 mL) and stir for 18 h at ambient temperature. Acidify with 1N aqueous HCl (5 mL), dilute, extract with ethyl ether (3×150 mL), basify aqueous with 1N aqueous NaOH, extract with DCM (3×50 mL), wash the organic extracts with brine, dry over MgSO4, filter and concentrate in vacuo. Purify by SCX chromatography to give crude the title compound as a yellow oil (380 mg).

후처리

  1. additiondilute
  2. extractionextract with ethyl ether (3×150 mL), basify aqueous with 1N aqueous NaOH
  3. extractionextract with DCM (3×50 mL)
  4. washwash the organic extracts with brine
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by SCX chromatography

출처 및 근거

ORD 기록
ord-4202df28a1e44c32977ebc6ea71649df
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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