Hydrochloric Acid → HCID 67323942, compound

HRID 1257631Notes

Reaction equation

HRID 1257631 reaction equation
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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67323870HCID 67323870, compound

Product 1

HCID 67323942HCID 67323942, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-cf4069e8da814df9958a994ea5583236
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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