Thiophene → HCID 18452754, compound

HRID 538084Notes

Reaction equation

HRID 538084 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:13])=[O:12].S1C=CC=C1>C1COCC1.[Pd]>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([N:17]2[CH2:16][CH2:15][N:14]([S:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)(=[O:13])=[O:12])[CH2:19][CH2:18]2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 8030ThiopheneHCID 2885971HCID 2885971, compound

Product 1

HCID 18452754HCID 18452754, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-naphthalenylsulfonyl)-4-(4-nitrophenyl)-piperazine (7.5 mmol) in THF (150 ml) was hydrogenated at 50° C. with Pd/C 10% (1 g) as a catalyst in the presence of thiophene solution (0.5 ml). After uptake of H2 (3 equiv.), the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from 2-propanol. The formed precipitate was filtered off, washed with 2-propanol and dried (55° C., vacuum), yielding 2.39 g (87%) of 1-(4-aminophenyl)-4-(2-naphthalenylsulfonyl)-piperazine (interm. 7).

Workup

  1. filtrationAfter uptake of H2 (3 equiv.), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from 2-propanol
  4. filtrationThe formed precipitate was filtered off
  5. washwashed with 2-propanol
  6. customdried (55° C., vacuum)

Sources & evidence

ORD record
ord-2db65382144c4066a53b568011317870
Source dataset
uspto-grants-2014_10
Patent number
US08865720B2

Reaction notes

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