Sodium amide → HCID 54152167, compound

HRID 1680664Notes

Reaction equation

HRID 1680664 reaction equation
[CH3:1][O:2][C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[CH:4]=1.[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22]Cl.[NH2-].[Na+].CO.C(Cl)(Cl)Cl>O>[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][N:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:3]([O:2][CH3:1])=[CH:4][C:5]2[CH:17]=[CH:16][CH:15]=[CH:14][C:6]1=2

Participants

6

Reactant 4

HCID 24533Sodium amide2×HCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 7842410-MethoxyiminostilbeneHCID 21584188Chloroform methanol

Product 1

HCID 54152167HCID 54152167, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml round bottom flask containing 9.87 g (0.044 moles) of 10-methoxy-5H-dibenz[b,f]azepine prepared in Example 3 and 13.9 g (0.088 moles) of 3-dimethylaminopropylchloride was evacuated for several days. Anhydrous toluene (250 ml) was added followed by 7.04 g (0.176 moles) of sodium amide. The heterogeneous solution was stirred at ambient temperature for a few minutes and then refluxed for 16 hours. After 16 hours of refluxing, tlc analysis of the reaction mixture (silica gel GF plates, methanol:chloroform 1:9; visualized under UV lamp and sulfuric acid-ceric sulfate spray) revealed that the reaction was complete and that no starting material remained. Enough water was added to slowly decompose the excess sodium amide. The dark-brown solution was placed in a 1 liter separatory funnel and extracted with four 250 ml portions of water. The organic phase was dried over anhydrous magnesium sulfate, charcoal was added and the mixture was filtered through a Celite pad. The filtrate was concentrated leaving a brown oil (12.6 g).

Workup

  1. customwas evacuated for several days
  2. additionAnhydrous toluene (250 ml) was added
  3. temperaturerefluxed for 16 hours
  4. temperatureAfter 16 hours of refluxing
  5. customThe dark-brown solution was placed in a 1 liter separatory funnel
  6. extractionextracted with four 250 ml portions of water
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate, charcoal
  8. additionwas added
  9. filtrationthe mixture was filtered through a Celite pad
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bc3a464ce9fd443190c8cb4d5e8e98ca
Source dataset
uspto-grants-1981_06
Patent number
US04275160

Reaction notes

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