Sodium Bicarbonate → HCID 18914206, compound

HRID 1292100Notes

Reaction equation

HRID 1292100 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][O:7][C:8]2[CH:25]=[CH:24][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][CH2:15]3)=[O:13])=[CH:10][C:9]=2[N+:26]([O-])=O)=[CH:4][CH:3]=1.O.[Sn](Cl)Cl.C(=O)([O-])O.[Na+]>C(O)C>[NH2:26][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:8]=1[O:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:30][CH:29]=1)[C:12]([N:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:18][CH2:19]1)=[O:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18914229HCID 18914229, compoundHCID 43835034Tin dichloride dihydrate

Product 1

HCID 18914206HCID 18914206, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To 85 ml of an ethanol solution containing 1-[4-(4-fluorobenzyloxy)-3-nitrobenzoyl]-4-isobutylpiperazine (HCl free form of Example 8) (17.5g) was added tin (II) chloride monohydrate (47.4 g) and the resulting mixture was stirred at 70° C. for 40 minutes. The mixture was poured into ice water, neutralized with sodium hydrogencarbonate, and then extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2 to 1:0), thereby yielding 14.5 g of 1-[3-amino-4-(4-fluorobenzyloxy)benzoyl]-4-isobutylpiperazine as a crystal. This compound (1.30 g) was converted into the corresponding hydrochloride salt as in the case of Example 8 which will be explained later, thereby yielding 1.51 g of the aimed compound. This compound is a crystal with a high hygroscopicity.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. concentrationconcentrated under a vacuum
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:2 to 1:0)

Sources & evidence

ORD record
ord-c91e87c7b52844b58a4a29ce7f6f5b65
Source dataset
uspto-grants-1998_05
Patent number
US05756505

Reaction notes

Loading…