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

HRID 1456329ノート

反応式

HRID 1456329 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 176Acetic Acid触媒HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-cfda118f6316423cb7fd4e88d4a83216
出典データセット
uspto-grants-1998_12
特許番号
US05843966

反応ノート

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