Acetic Acid → HCID 18430852, compound

HRID 1278609Notes

Reaction equation

HRID 1278609 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([CH:2]2[CH2:7][CH2:6][CH:5]([N:8]3[C:16](=[O:17])[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]3=[O:18])[CH2:4][CH2:3]2)[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 759941-BenzylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 18430852HCID 18430852, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)dione (3.78 g, 15.5 mmol), which was prepared according to the literature (J. Med. Chem., 1993, 1918), 1-benzylpiperazine (2.99 g/17.1 mmol) and AcOH (1.00 ml/17.1 mmol) in dichloroethane (50 ml) was added sodium triacetoxyborohydride (6.57 g/31.0 mmol) and the mixture was stirred for 2 days. The reaction mixture was poured into water (50 ml) and the mixture was extracted with dichloromethane (100 ml). The extract was washed with brine (50 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel/dichloromethane) to give a colorless oil (5.00 g/89%).

Workup

  1. extractionthe mixture was extracted with dichloromethane (100 ml)
  2. washThe extract was washed with brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH2 gel/dichloromethane)
  7. customto give a colorless oil (5.00 g/89%)

Sources & evidence

ORD record
ord-03bdbd75d8da44c9bc49b0ccc9236d3e
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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