Hydrochloric Acid → (2-Methoxy-5-tetrazol-1-ylbenzyl)(2-phenylpiperidin-3-yl)amine

HRID 1941515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941515
[C:1]1([C@H:7]2[C@@H:12]([NH2:13])[CH2:11][CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[N:27][N:26]=[N:25]2)=[CH:20][C:17]=1[CH:18]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:43]>ClCCl.C(O)(=O)C.C(O)C.CCOCC>[ClH:43].[ClH:43].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[N:27][N:26]=[N:25]2)=[CH:20][C:17]=1[CH2:18][NH:13][C@H:12]1[CH2:11][CH2:10][CH2:9][NH:8][C@H:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 9812908(2S,3S)-2-phenylpiperidin-3-amineHCID 105361692-Methoxy-5-tetrazol-1-yl-benzaldehyde

Produkt 1

HCID 127943(2-Methoxy-5-tetrazol-1-ylbenzyl)(2-phenylpiperidin-3-yl)amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidKatalysatorHCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of cis-2-phenylpiperidin-3-yl-amine (1.22 mmol) and 2-methoxy-5-tetrazol-1-yl-benzaldehyde (1.22 mmol) in dichloromethane (25 ml) was added sodium triacetoxy borohydride (1.7 mmol) and 2 drops of glacial acetic acid. The mixture was stirred at room temperature under nitrogen atmosphere for 18 h. The solvent was evaporated in vacuo and the residue quenched with 2N solution of sodium carbonate (20 ml) and extracted with ethyl acetate (3×50 ml). The organic layer was treated with 2N hydrochloric acid solution (20 ml) and the acidic portion basified with 2N sodium carbonate solution and extracted with dichloromethane (3×100 ml). The organic extracts were dried (MgSO4), filtered and concentrated to give a residue which was purified by FCC (dichloromethane/ethanol/ammonia--200:8:1) to give a white foam which was dissolved in ethanol (15 ml) and treated with 1M hydrochloric acid solution in ether (2.5 ml). The solvent was evaporated in vacuo and the resulting white solid triturated with isopropanol and filtered to afford the title compound. (49%). m.p. 242°-243° T.l.c. (Dichloromethane/ethanol/ammonia (200:8:1)) Rf 0.5

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue quenched with 2N solution of sodium carbonate (20 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. additionThe organic layer was treated with 2N hydrochloric acid solution (20 ml)
  5. extractionextracted with dichloromethane (3×100 ml)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue which
  10. customwas purified by FCC (dichloromethane/ethanol/ammonia--200:8:1)
  11. customto give a white foam which
  12. customThe solvent was evaporated in vacuo
  13. customthe resulting white solid triturated with isopropanol
  14. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-ee7d255191c9433da6c45bfc5e4e6219
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703240

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