Acetic Acid → AC-90179

HRID 354137노트

반응식

HRID 354137 반응식
[CH3:1][OH:2].CN[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[BH3-][C:21]#[N:22].[Na+].[C:24]([OH:27])(=O)[CH3:25]>CO.C(O)(=O)C>[CH3:1][O:2][C:6]1[CH:11]=[CH:10][C:9]([CH2:25][C:24]([N:22]([CH2:21][C:9]2[CH:10]=[CH:11][C:6]([CH3:5])=[CH:7][CH:8]=2)[CH:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)=[O:27])=[CH:8][CH:7]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 887MethanolHCID 7669N-MethylbenzylamineHCID 740491-Methyl-4-piperidoneHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 9799308AC-90179

시약·촉매·용매 1

HCID 10129899Acetic acid methanol용매

실험 절차

Methanol (50 ml) was added to an Erlenmeyer flask and acetic acid was added under stirring until pH 5. Methylbenzylamine (1.0 g, 8.8 mmol) and 1-Methyl-4-piperidone (1.1 g, 8.8 mmol) were added to a 100 ml round-bottomed flask and dissolved in the methanol/acetic acid (40 ml) solution previously made. The reaction mixture was stirred for 5 min and NaCNBH3 (0.83 g, 13.2 mmol) was added slowly under stirring. After 20 hours the reaction was concentrated and transferred to a separatory funnel containing dichloromethane and distilled water. The aqueous phase was made basic by addition of Na2CO3. The aqueous phase was extracted twice with dichloromethane. The combined organic layers were collected and dried with Na2SO4. Concentration afforded the title compound. Yield (crude): 98%. UV/MS 89/88 (M+ 353), tr (A, MS) 3.982.

후처리

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 5 min
  3. stirringunder stirring
  4. concentrationAfter 20 hours the reaction was concentrated
  5. customtransferred to a separatory funnel
  6. additioncontaining dichloromethane
  7. distillationdistilled water
  8. additionThe aqueous phase was made basic by addition of Na2CO3
  9. extractionThe aqueous phase was extracted twice with dichloromethane
  10. customThe combined organic layers were collected
  11. dry with materialdried with Na2SO4
  12. concentrationConcentration

출처 및 근거

ORD 기록
ord-d85096bf5ca24e459ba61de719fa2239
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756393B2

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