Water → HCID 44212983, compound

HRID 356147Notes

Reaction equation

HRID 356147 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:11](=[O:12])[CH:10]2[CH2:13][CH2:14][CH2:15][C:9]2=[N:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.Cl.C(O)C.[BH4-].[Li+].[Na+].[BH4-].O>ClCCl>[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:11](=[O:12])[CH:10]2[CH2:13][CH2:14][CH2:15][CH:9]2[NH:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 18940561HCID 18940561, compoundHCID 21887872Ethanol hydrochlorideHCID 131720935HCID 131720935, compound

Product 1

HCID 44212983HCID 44212983, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-(2,4-dichlorobenzyl)-2,3,9,10a-tetrahydrobenzo [b]cyclopenta[e][1,4]diazepin-10(1H)-one (0.9 g, 2.5 mmol) in dichloromethane (3 mL) was added 2.5N HCl-ethanol solution (1.5 mL), and the mixture was immediately concentrated under reduced pressure. The concentrate was dissolved in methanol (10 mL), to which was added sodium lithium borohydride (250 mg, 6.6 mmol). The mixture was stirred for 20 minutes at room temperature. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate three times. The organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, which was subjected to filtration. The filtrate was concentrated under reduced pressure, and the concentrate was purified by silica-gel column chromatography (hexane-ethyl acetate 6:1) to give 740 mg (yield 82%) of the titled compound. Amorphous.

Workup

  1. concentrationthe mixture was immediately concentrated under reduced pressure
  2. dissolutionThe concentrate was dissolved in methanol (10 mL), to which
  3. extractionwas subjected to extraction with ethyl acetate three times
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate, which
  6. filtrationwas subjected to filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe concentrate was purified by silica-gel column chromatography (hexane-ethyl acetate 6:1)

Sources & evidence

ORD record
ord-8e700e994060449dae35bbf4a3d65105
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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