Triethylamine → 1-{[(2-Chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}cyclohexanol

HRID 44744

반응식

HRID 44744 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([CH3:12])=[C:4]([CH3:13])[N:3]=1.Cl.[NH2:15][CH2:16][C:17]1([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:15][CH2:16][C:17]2([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:5]([CH3:12])=[C:4]([CH3:13])[N:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)HCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

생성물 1

HCID 575154311-{[(2-Chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}cyclohexanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

A 500 mL round bottom flask was charged with 2,4-dichloro-5,6-dimethyl-3-nitropyridine (6.00 g, 27.1 mmol), 1-aminomethyl-1-cyclohexanol hydrochloride (4.94 g, 29.8 mmol), and N,N-dimethylformamide (200 mL). The solution was cooled to 0° C. and triethylamine (8.31 mL, 59.6 mmol) was added dropwise. The solution was heated to 35° C. for 3 d. The volatiles were removed under reduced pressure and the resulting oil was partitioned between dichloromethane (300 mL) and water (50 mL). The organic layer was washed with water (50 mL) and brine (30 mL), dried over MgSO4, filtered, concentrated under reduced pressure, and dried under vacuum to yield 1-{[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}cyclohexanol that was used without further manipulation in the next step.

후처리

  1. temperatureThe solution was heated to 35° C. for 3 d
  2. customThe volatiles were removed under reduced pressure
  3. customthe resulting oil was partitioned between dichloromethane (300 mL) and water (50 mL)
  4. washThe organic layer was washed with water (50 mL) and brine (30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-81ac5fe2e5f84b67a570f755714c6630
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541438B2

연결된 노트

불러오는 중…