Acetic Acid → HCID 22342993, compound

HRID 584250Notes

Reaction equation

HRID 584250 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][CH:13]1[C:18](=[O:19])[NH:17][CH2:16][C:15](=[O:20])[NH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.CN(C)C=O>[CH2:1]([N:8]([C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=1)[CH2:12][CH:13]1[C:18](=[O:19])[NH:17][CH2:16][C:15](=[O:20])[NH:14]1)[CH3:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 712Formaldehyde2×HCID 5049666Sodium triacetoxyborohydride2×HCID 22342661HCID 22342661, compound

Product 1

HCID 22342993HCID 22342993, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-[3-(benzylamino)benzyl]-3,6-piperazinedione (0.45 g), 37% aqueous formaldehyde (81 mg), sodium triacetoxyborohydride (0.62 g) and acetic acid (175 mg) in a mixture of 1,2-dichloroethane (15 ml) and N,N-dimethylformamide (5 ml) was stirred for 5 hours at room temperature. Then additional 37% aqueous formaldehyde (0.1 ml), acetic acid (0.2 ml) and sodium triacetoxyborohydride (0.60 g) were added to the reaction mixture and the whole was stirred for further 2 hours. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of dichloromethane and methanol (10:1). The fractions containing the objective compound were collected and evaporated under reduced pressure. The resulting precipitates were collected by filtration and washed with isopropyl alcohol to give 2-[3-(N-benzyl-N-methylamino)benzyl]-3,6-piperazinedione (0.46 g) as colorless crystals.

Workup

  1. stirringthe whole was stirred for further 2 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel using
  4. additiona mixture of dichloromethane and methanol (10:1)
  5. additionThe fractions containing the objective compound
  6. customwere collected
  7. customevaporated under reduced pressure
  8. customThe resulting precipitates
  9. filtrationwere collected by filtration
  10. washwashed with isopropyl alcohol

Sources & evidence

ORD record
ord-01aed03fec8d4ec0ad90f65811710438
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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