Triethylamine → 1-[5,5-Bis(4-fluorophenyl)-4-pentenyl]-4-(phenylmethyl)-2-piperazinecarboxamide

HRID 1073158ノート

反応式

HRID 1073158 の反応式
Br[CH2:2][CH2:3][CH2:4][CH:5]=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[C:21]1([CH2:27][N:28]2[CH2:33][CH2:32][NH:31][CH:30]([C:34]([NH2:36])=[O:35])[CH2:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>CN(C)C=O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][CH2:4][CH2:3][CH2:2][N:31]2[CH2:32][CH2:33][N:28]([CH2:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:29][CH:30]2[C:34]([NH2:36])=[O:35])=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 142302664-Benzylpiperazine-2-carboxamideHCID 147225505-Bromo-1,1-bis-(4-fluorophenyl)pent-1-ene

生成物 1

HCID 198284451-[5,5-Bis(4-fluorophenyl)-4-pentenyl]-4-(phenylmethyl)-2-piperazinecarboxamide収率 61.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 74.2 parts of 1,1'-(5-bromo-1-penten-1-ylidene)bis[4-fluorobenzene], 43.8 parts of 4-(phenylmethyl)-2-piperazinecarboxamide, 38.9 parts of N,N-diethylethanamine and 1350 parts of N,N-dimethylformamide was stirred for 20 hours at 70° C. The reaction mixture was evaporated in vacuo and the residue was stirred in dichloromethane. The precipitate was filtered off. The filtrate was washed three times with 200 parts of water and once with 200 parts of a diluted ammonium hydroxide solution, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 58.9 parts (61.9%) of 1-[5,5-bis(4-fluorophenyl)-4-pentenyl]-4-(phenylmethyl)-2-piperazinecarboxamide as a residue (int. 33).

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. stirringthe residue was stirred in dichloromethane
  3. filtrationThe precipitate was filtered off
  4. washThe filtrate was washed three times with 200 parts of water
  5. dry with materialonce with 200 parts of a diluted ammonium hydroxide solution, dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

出典と根拠

ORDレコード
ord-8c7da48630174590aeb1df66ddb0215f
出典データセット
uspto-grants-1990_11
特許番号
US04968684

反応ノート

読み込み中…