4-Fluorobenzylamine → 4-[(tert-Butoxy)carbonyl]-1-(4-fluorobenzyl)-6-methylpiperazin-2-one

HRID 2109839Notes

Reaction equation

HRID 2109839 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14](=O)[CH3:15])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:14]([CH3:15])[N:23]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=2)[C:10](=[O:12])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57634645N-(tert-butoxycarbonyl)-N-(2-oxopropyl)glycine

Product 1

HCID 576346364-[(tert-Butoxy)carbonyl]-1-(4-fluorobenzyl)-6-methylpiperazin-2-one

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of N-[(tert-butoxy)carbonyl]-N-(2-oxopropyl)glycine (0.66 g, 2.87 mmol), 4-fluorobenzylamine (0.23 g, 1.87 mmol) in dichloroethane (14 mL) was stirred at room temperature for one hour. Sodium triacetoxyborohydride (0.79 g, 3.73 mmol) was added and the reaction mixture stirred at room temperature overnight. The resultant mixture was concentrated under vacuum. The residue was dissolved in DMF (12 mL), treated with EDC (0.55 g), and stirred at room temperature overnight. The resultant mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and dilute aqueous HCl. The organic extract was washed with brine (to pH 7), dried over anhydrous magnesium sulfate, filtered, and concentrated to provide the title compound.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. concentrationThe resultant mixture was concentrated under vacuum
  3. dissolutionThe residue was dissolved in DMF (12 mL)
  4. additiontreated with EDC (0.55 g)
  5. stirringstirred at room temperature overnight
  6. concentrationThe resultant mixture was concentrated under vacuum
  7. customThe residue was partitioned between ethyl acetate and dilute aqueous HCl
  8. extractionThe organic extract
  9. washwas washed with brine (to pH 7)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-837b931d0b304419bb637b12351b5263
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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