Sulfuric Acid → HCID 19261391, compound

HRID 1456926Notes

Reaction equation

HRID 1456926 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[Cl:12][CH2:13][CH2:14][C:15]([N:17]1[CH2:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[CH2:20][C:19]2[CH:28]=[CH:29][CH:30]=[CH:31][C:18]1=2)=O>O1CCCC1>[Cl:12][CH2:13][CH2:14][CH2:15][N:17]1[CH2:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[CH2:20][C:19]2[CH:28]=[CH:29][CH:30]=[CH:31][C:18]1=2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 22102511HCID 22102511, compound

Product 1

HCID 19261391HCID 19261391, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0M tetrahydrofuran solution of lithium aluminum hydride (9.8 ml) was introduced under a nitrogen atmosphere to a dry 100 ml three-necked roundbottom flask using a syringe. Concentrated sulphuric acid (0.264 ml) was cautiously added under cooling on an ice bath, and the resulting solution was stirred at room temperature for 1.5 hour. The above amide was dissolved in dry tetrahydrofuran (9.8 ml) and slowly added. The reaction mixture was stirred overnight. The reaction was quenched by addition of water (0.4 ml), 4N sodium hydroxide (0.4 ml) and water (1.2 ml), successively. The resulting mixture was filtered (hyflo) and the filtercake was washed with diethyl ether and ethyl acetate. The solvent was evaporated affording 5-(3-chloropropyl)-6, 11-dihydro-5H-dibenzo[b,e]azepine, which was used for further reaction without purification.

Workup

  1. temperatureunder cooling on an ice bath
  2. additionslowly added
  3. stirringThe reaction mixture was stirred overnight
  4. customThe reaction was quenched by addition of water (0.4 ml), 4N sodium hydroxide (0.4 ml) and water (1.2 ml)
  5. filtrationThe resulting mixture was filtered (hyflo)
  6. washthe filtercake was washed with diethyl ether and ethyl acetate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5aa1d47eb5de43c28c2aa6ff00dfde6a
Source dataset
uspto-grants-1998_12
Patent number
US05846968

Reaction notes

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