Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate → Tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylate

HRID 515316Notes

Reaction equation

HRID 515316 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 18538797Tert-butyl 4-[(4-nitrophenyl)sulfanyl]piperidine-1-carboxylate

Product 1

HCID 18538812Tert-butyl 4-(4-aminophenylthio)piperidine-1-carboxylateYield 108.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 4-(4-nitrophenylthio)piperidine-1-carboxylate (8.56 mmol, 2.8973 g) and palladium (3.77 mmol, 0.401 g) were combined in ethanol (30 mL) and the reaction mixture hydrogenated at 5 bar for 2 hours. The reaction mixture was filtered and concentrated under vacuum, reaction incomplete. Hydrogenation resumed with fresh palladium and left overnight. The reaction mixture was filtered and concentrated under vacuum to afford the title compound (2.86 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under vacuum, reaction incomplete
  3. waitleft overnight
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-01639aa61da4456a8295f845ae20d100
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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