Acetic Acid → HCID 9902382, compound

HRID 566879Notes

Reaction equation

HRID 566879 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]2[CH2:8][CH:9]=[C:10]([CH:12]=O)[CH:11]=[C:5]2[O:4][CH2:3]1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH2:26][CH2:25][N:24]([CH2:12][C:10]3[CH:9]=[CH:8][C:6]4[NH:7][C:2](=[O:1])[CH2:3][O:4][C:5]=4[CH:11]=3)[CH2:23][CH2:22]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 831131-(p-Tolyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 54197501HCID 54197501, compound

Product 1

HCID 9902382HCID 9902382, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-oxo-dihydro-2H-benzo[1,4]oxazine-7-carbaldehyde (0.5 g, 2.8 mmol), 1-(4-methyl-phenyl)-piperazine (0.5 g, 2.8 mmol), acetic acid (0.17 g, 2.8 mmol) and sodium triacetoxyborohydride (1.2 g, 5.9 mmol) in 20 mL of 1,2-dichloroethane is stirred at room temperature for 3 hours. The reaction is quenched with 50 mL of water, and the layers are separated. The aqueous phase is extracted with ethyl acetate (3×50 mL). The organic phases are combined and dried over sodium sulfate. Evaporation of the solvent gives a solid which is recrystallized twice from acetonitrile to give 0.31 g (33% yield) of 7-[4-(4-methyl-phenyl)-piperazin-1-ylmethyl]-4H-benzo[1,4]oxazine-3-one; mp 208-210° C.

Workup

  1. customThe reaction is quenched with 50 mL of water
  2. customthe layers are separated
  3. extractionThe aqueous phase is extracted with ethyl acetate (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. customgives a solid which
  7. customis recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-f959548f6c9e4548b1f9e07edb94748f
Source dataset
uspto-grants-2001_01
Patent number
US06177422B1

Reaction notes

Loading…