Sodium Carbonate → HCID 67515763, compound

HRID 2173296Notes

Reaction equation

HRID 2173296 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH:11]=[C:10]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].C([O-])([O-])=O.[Na+].[Na+]>CC(O)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH:10]([CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 86693014HCID 86693014, compound

Product 1

HCID 67515763HCID 67515763, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

A solution of tert-butyl 4-{[7-(methoxycarbonyl)-1-benzofuran-3-yl]methyl}piperazine-1-carboxylate (600 mg, 1.6 mmol) in 100 mL of HOAc was added 300 mg of Pd/C and the mixture was stirred at 65° C. under H2 atmosphere (50 psi) overnight. The reaction mixture was added Na2CO3 (aq.) to pH=8 in ice bath. The mixture was filtrated and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with silica gel chromatography to give tert-butyl 4-{[7-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-3-yl]methyl}piperazine-1-carboxylate. 1H-NMR (400 MHz, CDCL3) δ ppm 7.75 (d, J=8.0, 1 H), 7.38 (d, J=7.6, 1 H), 6.88 (t, J=8.0 Hz, 1H), 4.74 (t, J=9.0 Hz, 1H), 4.57 (dd, J=9.2, 6.2 Hz, 1H), 3.90 (s, 3H), 3.58-3.67 (m, 1H), 3.38-3.50 (m, 4H), 2.36-2.61 (m, 6H), 1.46 (s, 9H); MS m/z 377 (M+1)+.

Workup

  1. filtrationThe mixture was filtrated
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-a264afaacdd14cc7a19286dd81ea73c2
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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