Hydrochloric Acid → N-(3,4-dichlorophenyl)-4-(pyrrolidin-3-ylmethyl)piperazine-1-carboxamide

HRID 603206

反応式

HRID 603206 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([CH:20]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]3)=O)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].B.Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 57656707Tert-butyl 3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)carbonyl]pyrrolidine-1-carboxylate

生成物 1

HCID 57656782N-(3,4-dichlorophenyl)-4-(pyrrolidin-3-ylmethyl)piperazine-1-carboxamide収率 17.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of tert-butyl 3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)carbonyl]pyrrolidine-1-carboxylate (3.39 g, 7.19 mmol) in THF (60 ml) was added a 1M solution of borane in THF (21.6 ml, 21.6 mmol) and the reaction heated to reflux for 4 hours. The cooled reaction mixture was then cautiously quenched by addition of methanol then solvents removed in vacuo to give a white solid. To this was then added saturated HCl in methanol (150 ml) and heated to reflux for 1 hour. The reaction mixture was then evaporated to dryness, partitioned between 2M NaOH and DCM, extracted twice, combined organics dried (Na2SO4), filtered and evaporated to a colorless oil. This was then purified on Isco™ Companion (40 g column: 20% methanolic ammonia/DCM) to give the product N-(3,4-dichlorophenyl)-4-(pyrrolidin-3-ylmethyl)piperazine-1-carboxamide as a white foam (444 mg, 1.24 mmol, 17%).

後処理

  1. temperaturethe reaction heated
  2. temperatureto reflux for 4 hours
  3. customThe cooled reaction mixture
  4. customwas then cautiously quenched by addition of methanol
  5. customsolvents removed in vacuo
  6. customto give a white solid
  7. temperatureto reflux for 1 hour
  8. customThe reaction mixture was then evaporated to dryness
  9. custompartitioned between 2M NaOH and DCM
  10. extractionextracted twice
  11. dry with materialcombined organics dried (Na2SO4)
  12. filtrationfiltered
  13. customevaporated to a colorless oil
  14. customThis was then purified on Isco™ Companion (40 g column: 20% methanolic ammonia/DCM)

出典と根拠

ORDレコード
ord-1731eac883824e43b18c11bad1613d4e
出典データセット
uspto-grants-2011_03
特許番号
US07906645B2

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