Acetic Acid → 3-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one

HRID 1943029

반응식

HRID 1943029 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH:12]=O)[C:3]1=[O:14].[CH2:15]([N:22]1[CH2:26][CH2:25][C:24]([CH3:28])([NH2:27])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:15]([N:22]1[CH2:26][CH2:25][C:24]([NH:27][CH2:12][C:4]2[C:3](=[O:14])[N:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)([CH3:28])[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 49146281-Methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 105118971-Benzyl-3-methylpyrrolidin-3-amine

생성물 1

HCID 584159153-{[(1-benzyl-3-methylpyrrolidin-3-yl)amino]methyl}-1-methylquinolin-2(1H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde (956 mg, 5.11 mmol), 1-benzyl-3-methylpyrrolidin-3-amine (972 mg, 5.11 mmol), and acetic acid (0.877 ml, 15.32 mmol) were combined in CH2Cl2 (25 ml) and stirred for 30 min. Sodium triacetoxyborohydride (3248 mg, 15.32 mmol) was added and the reaction stirred for 2.5 hours before being partitioned between CH2Cl2 and satd. bicarb. The aqueous portion was extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The resulting material was carried on crude.

후처리

  1. stirringthe reaction stirred for 2.5 hours
  2. custombefore being partitioned between CH2Cl2 and satd
  3. extractionThe aqueous portion was extracted 3×CH2Cl2
  4. dry with materialthe organic portion dried (Na2SO4)
  5. concentrationthen concentrated in vacuo

출처 및 근거

ORD 기록
ord-bd05b3504fec40c392b54907932d2357
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389720B2

연결된 노트

불러오는 중…