Triethylamine → 3H-1,5-Benzodiazepine, 2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-

HRID 1782399ノート

反応式

HRID 1782399 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]([CH:26](O)[CH2:27][CH3:28])[C:10]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:9](=[CH:26][CH2:27][CH3:28])[C:10]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:7]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 100238171-[2,4-bis (4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol

生成物 1

HCID 102492283H-1,5-Benzodiazepine, 2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-収率 76%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of 1-[2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol (19.93 g, 50 mmol) and triethylamine (45 ml, 325 mmol) in dichloromethane (100 ml) under constant flow of argon, at 0° C., a solution of trifluoroacetic anhydride (21 ml, 150 mmol) in dichloromethane (50 ml) was added dropwise. The reaction mixture was stirred for another hour at 0° C. The solution was allowed to warm to room temperature. Methanol (66 ml) and tetrabutylammonium bromide (1.61 g, 5 mmol) were added successively. While strongly agitated NaOH (1 M, 660 ml) was added dropwise. Two phase system was agitated for two hours. The phases were separated and the water phase was extracted with dichloromethane (2×100 ml). The organic phase was dried over anhydrous Na2SO4 and the solvent was evaporated at reduced pressure. The crude product was suspended in isopropyl ether (150 ml) and filtered off the filtrate was evaporated at reduced pressure to give 14.44 g (76%) of the title compound as a brown resin.

後処理

  1. temperatureto warm to room temperature
  2. stirringTwo phase system was agitated for two hours
  3. customThe phases were separated
  4. extractionthe water phase was extracted with dichloromethane (2×100 ml)
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. customthe solvent was evaporated at reduced pressure
  7. filtrationfiltered off the filtrate
  8. customwas evaporated at reduced pressure

出典と根拠

ORDレコード
ord-1e0c4f3c945e4e7e8a516efbac4e0901
出典データセット
uspto-grants-2009_03
特許番号
US07498433B2

反応ノート

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