Ammonium Acetate → 1-(4-Aminopiperidin-1-yl)-3-phenylpropan-1-one

HRID 49446

반응식

HRID 49446 반응식
[C:1]1([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+]>CO>[C:1]1([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([NH2:24])[CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 178176121-(3-Phenylpropionyl)-4-ketopiperidine

생성물 1

HCID 167937721-(4-Aminopiperidin-1-yl)-3-phenylpropan-1-one수율 47%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To 3.2 g (13.8 mmol) of 135 in 125 mL of anhydrous methanol was added 21.3 g of ammonium acetate and 20 g of 3A molecular sieves. After stirring 30 min, 3.47 g (55.2 mmol) of sodium cyanoborohydride was added portionwise with stirring. After 3 hours, the mixture was gravity filtered, and the methanol evaporated under vacuum. The residue was partitioned between ice/HCl and ether. The acidic aqueous phase was extracted twice more with ether. The aqueous phase was made basic with ice and 50% aqueous NaOH. The mixture was extracted with CH2Cl2, dried, and evaporated under vacuum to give 1.5 g (47%) of the title amine 136. GC/MS indicated 100% purity with a molecular ion of 232.

후처리

  1. stirringwith stirring
  2. waitAfter 3 hours
  3. filtrationfiltered
  4. customthe methanol evaporated under vacuum
  5. customThe residue was partitioned between ice/HCl and ether
  6. extractionThe acidic aqueous phase was extracted twice more with ether
  7. extractionThe mixture was extracted with CH2Cl2
  8. customdried
  9. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-08ae6f502bb042ebb1e5e2dd2d00758b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706740B2

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