Triethylamine → 4-[4-[Bis(4-fluorophenyl)amino]butyl]-2-piperazinecarboxamide

HRID 1073157ノート

反応式

HRID 1073157 の反応式
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N: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.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH:22]1[C:27]([NH2:29])=[O:28].C(N(CC)CC)C>COCCO>[F:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2][N:24]2[CH2:25][CH2:26][NH:21][CH:22]([C:27]([NH2:29])=[O:28])[CH2:23]2)=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 3019914Piperazine-2-carboxamideHCID 14722551N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine

生成物 1

HCID 147225524-[4-[Bis(4-fluorophenyl)amino]butyl]-2-piperazinecarboxamide収率 55%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

実験手順

A mixture of 17.7 parts of N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine. 23.3 parts of 2-piperazinecarboxamide, 17.6 parts of N,N-diethylethanamine and 300 parts of 2-methoxyethanol was stirred for 48 hours at 70° C. The reaction mixture was evaporated and the residue was taken up in water and a small amount of methanol. The product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fraction was collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and acetonitrile (80:20 by volume). The product was filtered off and dried, yielding 12.82 parts (55.0%) of 4-[4-[bis-(4-fluorophenyl)amino]butyl]-2-piperazinecarboxamide; mp. 67.4° C. (int. 28).

後処理

  1. customThe reaction mixture was evaporated
  2. extractionThe product was extracted twice with dichloromethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe pure fraction was collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and acetonitrile (80:20 by volume)
  12. filtrationThe product was filtered off
  13. customdried

出典と根拠

ORDレコード
ord-9aee014c245547d5a7397f18b2c9af64
出典データセット
uspto-grants-1990_11
特許番号
US04968684

反応ノート

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