Ethanol → 1-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate

HRID 252882ノート

反応式

HRID 252882 の反応式
C([CH2:8][NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:13]1)C1C=CC=CC=1.CCO.C(OC(C)C)(=O)C>C(Cl)Cl>[CH3:8][NH:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 702EthanolHCID 7915Isopropyl AcetateHCID 57436142Biphenyl-2-ylcarbamic acid 1-[2-(benzylmethylamino)ethyl]piperidin-4-yl ester

生成物 1

HCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a Parr hydrogenation flask was added biphenyl-2-ylcarbamic acid 1-[2-(benzylmethylamino)ethyl]piperidin-4-yl ester (40 g, 0.09 mol; prepared as described in Preparation 3) and EtOH (0.5 L). The flask was flushed with nitrogen gas and palladium on activated carbon (15 g, 10 wt % (dry basis), 37% wt/wt) was added along with acetic acid (20 mL). The mixture was kept on the Parr hydrogenator under a hydrogen atmosphere (˜50 psi) for 3 hours. The mixture was then filtered and washed with EtOH. The filtrate was condensed and the residue was dissolved in a minimal amount of DCM. Isopropyl acetate (10 volumes) was added slowly to form a solid which was collected to provide 22.0 g of the title compound (70% yield). MS m/z: [M+H+] calcd for C21H27N3O2, 354.2; found, 354.3. Rf=2.96 min (10-70 ACN:H2O, reverse phase HPLC).

後処理

  1. customThe flask was flushed with nitrogen gas and palladium on activated carbon (15 g, 10 wt % (dry basis), 37% wt/wt)
  2. additionwas added along with acetic acid (20 mL)
  3. customfor 3 hours
  4. filtrationThe mixture was then filtered
  5. washwashed with EtOH
  6. customcondensed
  7. customto form a solid which
  8. customwas collected

出典と根拠

ORDレコード
ord-c3500700ddf54c569e772ef1fc1c1810
出典データセット
uspto-grants-2011_01
特許番号
US07868175B2

反応ノート

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