HCID 20144286, compound → HCID 14155428, compound

HRID 648927Notes

Reaction equation

HRID 648927 reaction equation
[CH3:1][N:2]1[CH2:26][CH2:25][N:5]2[C:6]3[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=3[CH2:8][N:9]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:11]([C:18]([O-])=[O:19])=[C:10]3[CH:4]2[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]1[CH2:26][CH2:25][N:5]2[C:6]3[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=3[CH2:8][N:9]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:11]([CH2:18][OH:19])=[C:10]3[CH:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 20144286HCID 20144286, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14155428HCID 14155428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.4 g of methyl, 1,3,4,16b-tetrahydro-2-methyl-2H,10H-indolo[2,1-c]pyrazino[1,2-a][1,4]benzodiazepine-16-carboxylate in 100 ml tetrahydrofuran is added 1 g of lithium aluminum hydride in small portions over a 10 minute period maintaining the temperature of the reaction below 25°. On completion of the addition the reaction is heated at reflux temperature for 4 hours. On cooling to room temperature the reaction mixture is quenched by the cautious dropwise addition of 0.65 ml of water, then 0.65 ml 15% NaOH solution followed by 1.95 ml water. The reaction mixture is filtered and the filter cake washed thoroughly with 100 ml of methylene chloride. The filtrate is evaporated to dryness under reduced pressure to yield 1,3,4,16b-tetrahydro-2-methyl-16-hydroxymethyl-2H,10H-indolo[2,1-c]pyrazino[1,2-a][1,4]benzodiazepine as an oil which, after crystallization from ether, has mp 184°-189°.

Workup

  1. temperaturemaintaining
  2. customthe temperature of the reaction below 25°
  3. additionOn completion of the addition the reaction
  4. temperatureis heated
  5. temperatureat reflux temperature for 4 hours
  6. customis quenched by the cautious dropwise addition of 0.65 ml of water
  7. filtrationThe reaction mixture is filtered
  8. washthe filter cake washed thoroughly with 100 ml of methylene chloride
  9. customThe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b0bc195184e149e4b936e3bbe7f92ac5
Source dataset
uspto-grants-1988_04
Patent number
US04737496

Reaction notes

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