tert-Butyl 4-(2-chloro-5-fluoro-4-nitrobenzylidene)piperidine-1-carboxylate → Tert-butyl 4-(4-amino-2-chloro-5-fluorobenzyl)piperidine-1-carboxylate

HRID 515302Notes

Reaction equation

HRID 515302 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([N+:22]([O-])=O)[C:19]([F:25])=[CH:18][C:3]=1[CH:4]=[C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1>C(O)C.[Pt](=O)=O>[NH2:22][C:20]1[C:19]([F:25])=[CH:18][C:3]([CH2:4][CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)=[C:2]([Cl:1])[CH:21]=1

Participants

4

Reactant 1

HCID 67194189tert-Butyl 4-(2-chloro-5-fluoro-4-nitrobenzylidene)piperidine-1-carboxylate

Product 1

HCID 67194509Tert-butyl 4-(4-amino-2-chloro-5-fluorobenzyl)piperidine-1-carboxylateYield 114.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×

Procedure

A slurry of platinum (IV) oxide (0.074 mmol, 16.84 mg) in ethanol was added to a solution of tert-butyl 4-(2-chloro-5-fluoro-4-nitrobenzylidene)piperidine-1-carboxylate (1.483 mmol, 550 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-2-chloro-5-fluorobenzyl)piperidine-1-carboxylate (580 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-4cafd27267124ca4ab336bfa170c2738
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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