Hydrochloric Acid → HCID 67323942、化合物

HRID 1257631ノート

反応式

HRID 1257631 の反応式
C([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])[C:17](=[O:32])[CH2:16]1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])[C:17](=[O:32])[CH2:16]1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 67323870HCID 67323870、化合物

生成物 1

HCID 67323942HCID 67323942、化合物収率 75%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of racemic 4-(benzhydryl-amino)-1-(2,4-dimethoxy-benzyl)-piperidin-2-one (3.30 g, 7.80 mmol), 10% Pd on carbon (410 mg, 0.39 mmol) and 2M aqueous HCl (4 mL, 8.15 mmol) in ethanol (150 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 23 hours. The reaction mixture was filtered through Celite® which was washed with ethanol, and the filtrate concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel (gradient: 2M NH3 in methanol solution in DCM) to afford 1.53 g (75%) of 4-amino-1-(2,4-dimethoxy-benzyl)-piperidin-2-one as an oil. LCMS (Method I, ESI): RT=1.57 min, m+H=265.3; 1H NMR (400 MHz, CDCl3) δ: 7.15 (d, 1H), 6.46-6.42 (m, 2H), 4.56 (m, 2H), 3.80 (m, 6H), 3.33 (dt, 1H), 3.22 (m, 2H), 2.69 (ddd, 1H), 2.21 (dd, 1H), 1.94 (m, 1H), 1.59 (dtd, 1H).

後処理

  1. filtrationThe reaction mixture was filtered through Celite® which
  2. washwas washed with ethanol
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe resulting residue was purified by column chromatography on silica gel (gradient: 2M NH3 in methanol solution in DCM)

出典と根拠

ORDレコード
ord-cf4069e8da814df9958a994ea5583236
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

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