Hydrazine hydrate (1:1) → tert-Butyl 4-(4-aminobenzyl)piperidine-1-carboxylate

HRID 412906Notes

Reaction equation

HRID 412906 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18538556HCID 18538556, compound

Product 1

HCID 21876872tert-Butyl 4-(4-aminobenzyl)piperidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To the solution of 1-tert-butoxycarbonyl-4-(4-nitrobenzyl)piperidine (4.53 g, 14.2 mmol) in methanol-tetrahydrofuran (1:1, 100 mL) were added activated carbon (2 g) and anhydrous ferric chloride (250 mg). To the mixture was added hydrazine monohydrate (5.64 mL), and the mixture was heated for 26 hours under ref lux. The reaction mixture was cooled to room temperature, the activated carbon was filtered off. The activated carbon was washed with metahnol. The filtrate and washings were combined, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=2/3) to give the titled compound (4 g) as colorless powdery crystals.

Workup

  1. temperaturethe mixture was heated for 26 hours under ref lux
  2. filtrationthe activated carbon was filtered off
  3. washThe activated carbon was washed with metahnol
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-c9ddf5b5650a42d0896f2c02b4e31953
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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