Hydrazine hydrate (1:1) → 1-Boc-3-(aminomethyl)piperidine

HRID 1931304Notes

Reaction equation

HRID 1931304 reaction equation
O.NN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1>C(O)C>[NH2:6][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86649437tert-Butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]piperidine-1-carboxylate

Product 1

HCID 27564831-Boc-3-(aminomethyl)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (1 mL, 20.58 mmol) was added to an ethanol (20 mL) solution of the compound (1.45 g, 4.21 mmol) synthesized in (1), and the mixture was stirred at room temperature for 24 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was re-suspended in ethanol, and allowed to stand under ice-cooled conditions. After filtration, the filtrate was concentrated under reduced pressure to obtain the target (823 mg, 91%).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. temperaturecooled conditions
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto obtain the target (823 mg, 91%)

Sources & evidence

ORD record
ord-c0d8502e156249f7b5d589fc5360a9ef
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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