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

HRID 1456329

반응식

HRID 1456329 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 176Acetic Acid촉매HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of cis-2-phenyl-piperidin-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 (1.70 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%).

후처리

  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

출처 및 근거

ORD 기록
ord-cfda118f6316423cb7fd4e88d4a83216
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843966

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