Silica → HCID 53788591, compound

HRID 362788Notes

Reaction equation

HRID 362788 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:23]([C:25]3[CH:30]=[CH:29][C:28]([NH2:31])=[C:27]([N+:32]([O-])=O)[CH:26]=3)=[O:24])[CH2:16][CH2:15]2)=[O:12])=[CH:4][C:3]=1[Cl:35].O=[Si]=O>O1CCCC1.[Pt]>[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:23]([C:25]3[CH:30]=[CH:29][C:28]([NH2:31])=[C:27]([NH2:32])[CH:26]=3)=[O:24])[CH2:16][CH2:15]2)=[O:12])=[CH:4][C:3]=1[Cl:35]

Participants

5

Reactant 2

HCID 24261SilicaHCID 54021504HCID 54021504, compound

Product 1

HCID 53788591HCID 53788591, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (11) (8.2 g) in tetrahydrofuran (150 ml) was hydrogenated with platinum on activated carbon (5%) (2 g) as a catalyst. After uptake of H2 (3 equiv), the catalyst was filtered off over dicalite and the filtrate was evaporated. The residue was diluted with water and this mixture was extracted twice with CH2Cl2. The separated organic layer was washed with water, dried over MgSO4, filtered and the solvent evaporated. The residue (8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 92/8). The pure fractions were collected and the solvent was evaporated. The residue (7.5 g) was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 5.43 g (70.5%) of 1-[4-(3,4-diaminophenyl)-4-oxobutyl]-4-piperidinyl 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylate; mp. 173.4° C. (intermediate 12).

Workup

  1. customthe filtrate was evaporated
  2. additionThe residue was diluted with water
  3. extractionthis mixture was extracted twice with CH2Cl2
  4. washThe separated organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue (8 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 92/8)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue (7.5 g) was crystallized from CH3CN
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-126a8a1579f0427794c81fe43c03957b
Source dataset
uspto-grants-1999_02
Patent number
US05872131

Reaction notes

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