Tert-butyl 4-(3-chloro-4-nitrobenzylidene)piperidine-1-carboxylate → Tert-butyl 4-(4-amino-3-chlorobenzyl)piperidine-1-carboxylate

HRID 515312Notes

Reaction equation

HRID 515312 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1>C(O)C.[Pt](=O)=O>[NH2:22][C:21]1[CH:20]=[CH:19][C:4]([CH2:5][CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:10][CH2:11]2)=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 67192823Tert-butyl 4-(3-chloro-4-nitrobenzylidene)piperidine-1-carboxylate

Product 1

HCID 67192609Tert-butyl 4-(4-amino-3-chlorobenzyl)piperidine-1-carboxylateYield 83.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×

Procedure

A slurry of platinum (IV) oxide (0.037 mmol, 8.37 mg) in ethanol was added to a solution of tert-butyl 4-(3-chloro-4-nitrobenzylidene)piperidine-1-carboxylate (0.737 mmol, 260 mg) in ethanol and the resulting suspension was hydrogenated at 3 bar for 45 minutes. The reaction mixture was filtered through celite, washing with ethanol. The filtrate was concentrated under vacuum to afford the intermediate tert-butyl 4-(4-amino-3-chlorobenzyl)piperidine-1-carboxylate (200 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashing with ethanol
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-e003d904d26b49859fa2bb3ccbafc543
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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