HCID 22342927, compound → HCID 22342661, compound

HRID 584249Notes

Reaction equation

HRID 584249 reaction equation
C(O[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][CH:13]1[NH:18][C:17](=[O:19])[CH2:16][NH:15][C:14]1=[O:20])=O)(C)(C)C>FC(F)(F)C(O)=O>[CH2:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][CH:13]1[C:14](=[O:20])[NH:15][CH2:16][C:17](=[O:19])[NH:18]1)[C:9]1[CH:10]=[CH:11][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 22342927HCID 22342927, compound

Product 1

HCID 22342661HCID 22342661, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-[3-(tert-butoxycarbonylamino)benzyl]-2,5-piperazinedione. (0.75 g) in trifluoroacetic acid (10 ml) was stirred for 4 hours at room temperature. After removal of the solvent by evaporation, the residue was dissolved in a mixture of dichloromethane (10 ml) and methanol (3 ml) and thereto benzaldehyde (0.742 g) and sodium triacetoxyborohydride (2.11 g) were added. The whole was stirred for 2 hours at room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (25:1). The fractions containing the objective compound were collected and triturated with isopropyl alcohol to give 2-[3-(benzylamino)benzyl]-3,6-piperazinedione (0.43 g) as colorless crystals.

Workup

  1. customAfter removal of the solvent
  2. customby evaporation
  3. dissolutionthe residue was dissolved in a mixture of dichloromethane (10 ml) and methanol (3 ml)
  4. additionbenzaldehyde (0.742 g) and sodium triacetoxyborohydride (2.11 g) were added
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of dichloromethane and methanol (25:1)
  8. additionThe fractions containing the objective compound
  9. customwere collected
  10. customtriturated with isopropyl alcohol

Sources & evidence

ORD record
ord-3945ebe4284444d4830a865baf372d8e
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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