Phenethylamine → 2-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl Ester

HRID 987094ノート

反応式

HRID 987094 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH:16]([CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20])[CH2:15][CH2:14][CH2:13][CH:12]1[C:23](O)=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([NH2:34])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH:12]([C:23](=[O:24])[NH:34][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 543519096-(2,2-Dimethoxy-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester2 回

生成物 1

HCID 545104932-(2,2-Dimethoxy-ethyl)-6-phenethylcarbamoyl-piperidine-1-carboxylic Acid Benzyl Ester収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

6-(2,2-Dimethoxy-ethyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester (Compound 238, 0.335 g, 0.96 mmol) and phenethyl amine (0.14 g, 1.15 mmol) were dissolved CH2Cl2 (20 mL). HOBt (0.156 g, 1.15 mmol) was added followed by EDC.HCl (0.221 g, 1.15 mmol). The reaction was stirred at room temperature for 18 hours. Saturated NaHCO3 solution (25 mL) was added and then extracted with CHCl3 (2×50 mL). The combined organic layers were dried over Na2SO4, and then concentrated. Flash chromatographic purification of the residue (1:1 EtOAc/hexanes) gave Compound 239 (0.374 g, 86%). Rf=0.47 (1:1 EtOAC/hexanes).

後処理

  1. extractionextracted with CHCl3 (2×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customFlash chromatographic purification of the residue (1:1 EtOAc/hexanes)

出典と根拠

ORDレコード
ord-dca6f6e4208b4f12b57989d2c6f8a457
出典データセット
uspto-grants-2003_10
特許番号
US06630472B1

反応ノート

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