Hydrochloric Acid → HCID 67323942, 화합물

HRID 1257631노트

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HRID 1257631 반응식
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

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 67323870HCID 67323870, 화합물

생성물 1

HCID 67323942HCID 67323942, 화합물수율 75%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cf4069e8da814df9958a994ea5583236
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461328B2

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