Methylamine → 7,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 1963799노트

반응식

HRID 1963799 반응식
[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH:14]=O)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[CH3:21][NH2:22].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][NH:22][CH3:21])[CH2:10][CH2:11][C:5]=2[CH:4]=1

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 201441843-(7,8-Dimethoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propionaldehyde

생성물 1

HCID 100172197,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one수율 98.8%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Dissolve 50 g (0.18 mol) of 3-(7,8-dimethoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propionaldehyde in 625 mL of methanol. Cool the resulting solution to 0° C. Then add 62.5 mL (0.81 mol; 4.5 equivalents) of 40% aqueous methylamine solution. Stir for one hour at 0° C., and then add 7.5 g (0.2 mol; 1.1 equivalents) of NaBH4. Stir for 30 minutes at 0° C. and then stir for 12 hours at ambient temperature. Evaporate off the methanol. The residue is taken up in aqueous hydrochloric acid solution (1N), washed with ethyl acetate and then the aqueous phase is brought to pH=8 by adding 20% sodium hydroxide solution and extracted with dichloromethane. The organic, phase is washed with water, dried over MgSO4, filtered and then evaporated to dryness to obtain 52 g of an oil.

후처리

  1. stirringStir for 30 minutes at 0° C.
  2. stirringstir for 12 hours at ambient temperature
  3. customEvaporate off the methanol
  4. washwashed with ethyl acetate
  5. additionby adding 20% sodium hydroxide solution
  6. extractionextracted with dichloromethane
  7. washThe organic, phase is washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness

출처 및 근거

ORD 기록
ord-570f0427420f41b193ed945e2495abfa
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415468B2

반응 노트

불러오는 중…