Aluminium lithium hydride → HCID 14390915, compound

HRID 2292280Notes

Reaction equation

HRID 2292280 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[C:8]([N:16]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][CH:26]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:19][CH2:18][N:17]1[C:41](=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCOCC>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH:26]([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[CH2:25][CH2:24][CH2:23][N:20]2[CH2:21][CH2:22][N:16]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:17]([CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:18][CH2:19]2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21277230HCID 21277230, compound

Product 1

HCID 14390915HCID 14390915, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To lithium aluminum hydride (21 g) in ether (150 ml) was added 1,2-dibenzoyl-5-[4,4-bis(4-fluorophenyl)butyl]hexahydro-1H-1,2,5-triazepine hydrochloride (34.4 g) slowly in small portions. The mixture was stirred and heated under reflux with protection from moisture for 22 hours. The reaction was quenched with 10% sodium hydroxide and water. The resulting hydroxides were collected on a filter and washed well with ether. The filtrate and washings were evaporated to a syrup, wt. 30.4 g. The syrup was dissolved in acetone and the solution was decolorized (Nuchar). The solution was concentrated and a solution of fumaric acid (6.7 g) in acetone (800 ml) was added. The resulting solution was boiled down until crystallization occurred. After cooling, the crude product was collected on a filter and washed with acetone; wt. 32.9 g. Recrystallization from methanol-ether gave 25.3 g (68%) of pure titled product as the fumarate salt (1:1), mp=184°-185°.

Workup

  1. temperatureheated
  2. temperatureunder reflux with protection from moisture for 22 hours
  3. customThe reaction was quenched with 10% sodium hydroxide and water
  4. customThe resulting hydroxides were collected on
  5. filtrationa filter
  6. washwashed well with ether
  7. customThe filtrate and washings were evaporated to a syrup, wt. 30.4 g
  8. dissolutionThe syrup was dissolved in acetone
  9. concentrationThe solution was concentrated
  10. additiona solution of fumaric acid (6.7 g) in acetone (800 ml) was added
  11. customThe resulting solution was boiled down until crystallization
  12. temperatureAfter cooling
  13. customthe crude product was collected on
  14. filtrationa filter
  15. washwashed with acetone
  16. customRecrystallization from methanol-ether

Sources & evidence

ORD record
ord-6ec70ab5e70a4acea0d4e94a0ef8a99b
Source dataset
uspto-grants-1989_01
Patent number
US04801706

Reaction notes

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