Aluminium lithium hydride → HCID 20200365, compound

HRID 543629Notes

Reaction equation

HRID 543629 reaction equation
C(O[C:4](=O)[NH:5][CH2:6][CH2:7][CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][C:11]2[CH:26]=[CH:27][CH:28]=[N:29][C:10]1=2)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:20]1([CH:13]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:9]([CH2:8][CH2:7][CH2:6][NH:5][CH3:4])[C:10]3[N:29]=[CH:28][CH:27]=[CH:26][C:11]=3[NH:12]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 54481943HCID 54481943, compound

Product 1

HCID 20200365HCID 20200365, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.4 g (0.0035 mole) of N-[3-[6-phenyl)-11H-pyrido[2,3-b][1,4]benzodiazepine-11-yl]propyl]carbamic acid ethyl ester (from Example 29) in tetrahydrofuran under nitrogen gas was added 0.4 g (0.0105 mole) of lithium aluminum hydride and slight exothermic reaction occurred. The mixture was cooled to prevent overheating. The mixture was stirred at reflux temperature for 16 hr. Thin layer chromatography indicated only partial conversion had occurred. An additional 0.4 g (0.0105 mole) of lithium aluminum hydride was added and the mixture refluxed overnight. Thin-layer chromatography indicated the product was predominantly the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. temperatureat reflux temperature for 16 hr
  3. temperaturethe mixture refluxed overnight

Sources & evidence

ORD record
ord-e93fe490b91644ceae914d59c6c4c434
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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