Hydrochloric Acid → 2-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile

HRID 896254노트

반응식

HRID 896254 반응식
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl>C1COCC1.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[NH2:1][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)[C:9]([O:21][CH3:22])=[CH:8][C:5]=1[C:6]#[N:7]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 223496205-Methoxy-4-[(1-methylpiperidin-4-yl)methoxy]-2-nitrobenzonitrile

생성물 1

HCID 223496642-Amino-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile수율 75.5%

시약·촉매·용매 3

HCID 5963Benzyltrimethylammonium chloride촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

2-nitro-4-(1-methylpiperidin-4-ylmethoxy)-5-methoxybenzonitrile (1.1 g, 3.6 mmol) in THF (20 ml) in presence of benzyltrimethylammonium chloride (334 mg, 1.8 mmol) was treated by a slow addition of Na2S2O4 (3.1 g, 18 mmol) in water (20 ml). After 0.5 h, HCl (6N, 20 ml) was added to the mixture, which was stirred at 60° C. for 5 h. The mixture was cooled to room temperature, extracted with ethylacetate. The aqueous phase was made basic with Na2 CO3 (solid), and extracted with ethylacetate. The organic phase was dried over MgSO4, concentrated, to give a yellow solid (748 mg, 75%) of title compound.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethylacetate
  3. extractionextracted with ethylacetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-274159f323c348ee8e4688369550225b
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919338B2

반응 노트

불러오는 중…