Tetrahydrofuran → HCID 13477808, compound

HRID 371080Notes

Reaction equation

HRID 371080 reaction equation
[CH2:1]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][N:10]2[C:18]3[C:23]([CH:24]=[C:9]2[C:8]1=O)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[OH-].[Na+]>O>[CH2:1]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][N:10]2[C:18]3[C:23]([CH:24]=[C:9]2[CH2:8]1)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 13477807HCID 13477807, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13477808HCID 13477808, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 8 g of 11-hexyl-6H-indolo[2,1-c][1,4]benzodiazepin-12(11H)-one, the product of Example 12, 1.5 g of lithium aluminum hydride and 100 ml of THF were added and the mixture was heated to reflux for 4 hours. The reaction mixture was cooled to 0° C. and then 1.5 ml of water, 1.5 ml of 15% NaOH solution and 4.5 ml of water were sequentially added. The resultant white solid was filtered off and the solvent was stripped off to give the titled compound. Recrystallization from i-PrOH gave a colorless solid, mp 45° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationThe resultant white solid was filtered off

Sources & evidence

ORD record
ord-744542b1550747f0bbc36e29dfd8a51c
Source dataset
uspto-grants-1985_07
Patent number
US04529724

Reaction notes

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