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

HRID 603206

Reaktionsgleichung

Reaktionsgleichung von HRID 603206
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 57656782N-(3,4-dichlorophenyl)-4-(pyrrolidin-3-ylmethyl)piperazine-1-carboxamideAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1731eac883824e43b18c11bad1613d4e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906645B2

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