Hydrochloric Acid → HCID 19045712, compound

HRID 1781517Notes

Reaction equation

HRID 1781517 reaction equation
[C:1]1([C:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([CH2:22][NH:23][S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)C.[Pd]>[NH2:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][NH:11][CH2:10][CH2:9][CH2:8][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:22][NH:23][S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19045738HCID 19045738, compound

Product 1

HCID 19045712HCID 19045712, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4,4-diphenyl-1-(3-nitrobenzylamino)-5-(tosylamino)pentane (0.17 g) in ethanol (10 ml) was added hydrochloric acid (0.1 ml) as well as 10% palladium-on-carbon (80 mg) and the mixture was subjected to catalytic hydrogenation at atmospheric temperature and pressure. The catalyst was then removed from the reaction mixture and the filtrate was concentrated to dryness. The group was dissolved in water and the solution was made basic with aqueous ammonia. The resulting precipitate was recovered by filtration, rinsed with water, and dried to provide the title compound (0.12 g) as light-tan powder.

Workup

  1. customThe catalyst was then removed from the reaction mixture
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe group was dissolved in water
  4. filtrationThe resulting precipitate was recovered by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-39787aa98c37454d9bfacfbb145e24ab
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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