4-Methylpiperidine → 9-Bromo-6-(4-methyl-1-piperidinyl)-1,2-dihydrobenzo[b]pyrrolo-[3,2,1-jk][1,4]benzodiazepine

HRID 4016

反応式

HRID 4016 の反応式
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH2:17][CH2:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9](=O)[NH:10][C:4]=2[CH:3]=1.[CH3:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>[Ti](Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH2:17][CH2:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9]([N:24]3[CH2:25][CH2:26][CH:21]([CH3:20])[CH2:22][CH2:23]3)=[N:10][C:4]=2[CH:3]=1

参加物

5

反応物 2

HCID 693814-MethylpiperidineHCID 138232839-Bromo-1,2dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one

生成物 1

HCID 138233039-Bromo-6-(4-methyl-1-piperidinyl)-1,2-dihydrobenzo[b]pyrrolo-[3,2,1-jk][1,4]benzodiazepine収率 83%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 1140Toluene溶媒

実験手順

A mixture of 4.73 g (0.0150 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1000 ml of toluene was heated under nitrogen, with stirring, until a solution resulted. Then there was added 14.9 g (0.150 mole) of 4-methylpiperidine, followed by 8.54 g (0.045 mole) of titanium tetrachloride. The mixture was refluxed for 3 hours, cooled to room temperature and filtered. The filtrate was stirred with 500 ml of 2N sodium hydroxide solution for 15 minutes and the layers were separated. The aqueous phase was extracted with 250 ml of toluene. The toluene layers were combined, washed once with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to an oil which solidified. The solid was triturated twice with hexane to afford 4.9 g (83%) of product. Recrystallization from ethyl acetate provided the analytical sample, mp 177°-179° C.

後処理

  1. temperaturewas heated under nitrogen
  2. customresulted
  3. temperatureThe mixture was refluxed for 3 hours
  4. filtrationfiltered
  5. stirringThe filtrate was stirred with 500 ml of 2N sodium hydroxide solution for 15 minutes
  6. customthe layers were separated
  7. extractionThe aqueous phase was extracted with 250 ml of toluene
  8. washwashed once with 2N sodium hydroxide solution, twice with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to an oil which
  12. customThe solid was triturated twice with hexane

出典と根拠

ORDレコード
ord-2914492a9d1346ff9a2310b39c27edd6
出典データセット
uspto-grants-1988_02
特許番号
US04723007

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