Thiophene → HCID 53754573, compound

HRID 1769683Notes

Reaction equation

HRID 1769683 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12](=[O:22])[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH:20]=[O:21])[CH2:16][CH2:15]2)=[C:6]([Cl:23])[CH:5]=1)([O-])=O.S1C=CC=C1.[NH4+].[OH-]>CO.[Pt].C(Cl)Cl>[NH2:1][C:4]1[CH:5]=[C:6]([Cl:23])[C:7]([NH:11][C:12](=[O:22])[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH:20]=[O:21])[CH2:16][CH2:15]2)=[C:8]([Cl:10])[CH:9]=1

Participants

7

Reactant 3

HCID 8030ThiopheneHCID 14923Ammonium HydroxideHCID 53854495HCID 53854495, compound

Product 1

HCID 53754573HCID 53754573, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-nitro-2,6-dichlorophenyl)-4-formyl-1-piperazineacetamide (1.79 g crude) was suspended in methanol (50 mL) containing 4% methanolic thiophene (0.5 mL) and 5% platinum on charcoal catalyst (900 mg). This was hydrogenated using a Parr apparatus for 30 minutes at 50° C. and 26 psi. After filtration and the removal of solvent in vacuo, the filtrate yielded 1.38 g of crude residue. This was subjected to flash chromatography on deactivated silica gel (from a slurry of 300 g of silica gel in methylene chloride containing 3.4 mL of conc. NH4OH). The product was eluted with CH2Cl2 :MeOH:NH4OH 98.8:1.0:0.2 yielding 590 mg of III an off-white solid. This was triturated in methylene chloride-ether to yield a white solid (520 mg, 39% yield).: m.p.>220° C. (dec.).

Workup

  1. customfor 30 minutes
  2. customat 50° C.
  3. filtrationAfter filtration
  4. customthe removal of solvent in vacuo
  5. customthe filtrate yielded 1.38 g of crude residue
  6. washThe product was eluted with CH2Cl2 :MeOH:NH4OH 98.8:1.0:0.2 yielding 590 mg of III an off-white solid
  7. customThis was triturated in methylene chloride-ether

Sources & evidence

ORD record
ord-f8c900d661c44be09050d2c2b1cac2b7
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

Loading…