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

HRID 1963799ノート

反応式

HRID 1963799 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-570f0427420f41b193ed945e2495abfa
出典データセット
uspto-grants-2013_04
特許番号
US08415468B2

反応ノート

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