Sodium Carbonate → 1,2-Dibenzoyl-5-[4,4-bis(4-fluorophenyl)butyl]-hexahydro-1H-1,2,5-triazepin

HRID 2292278Notes

Reaction equation

HRID 2292278 reaction equation
Cl.[C:2]([N:10]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]([C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[CH2:39][CH2:40][CH2:41]Br)=[CH:34][CH:33]=1>CN(C)C=O>[C:2]([N:10]1[CH2:16][CH2:15][N:14]([CH2:41][CH2:40][CH2:39][CH:38]([C:35]2[CH:34]=[CH:33][C:32]([F:31])=[CH:37][CH:36]=2)[C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[CH2:13][CH2:12][N:11]1[C:17](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 937631,1'-(4-Bromobutylidene)bis[4-fluorobenzene]HCID 212772321,2-dibenzoylhexahydro-1H-1,2,5-triazepine hydrochloride

Product 1

HCID 143909131,2-Dibenzoyl-5-[4,4-bis(4-fluorophenyl)butyl]-hexahydro-1H-1,2,5-triazepin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 1,2-dibenzoylhexahydro-1H-1,2,5-triazepine hydrochloride (13.0 g), powdered anhydrous sodium carbonate (17.8 g) in N,N-dimethylformamide (100 ml, dried over 4A molecular sieves) under a purging nitrogen atmosphere was added 4,4-bis(4-fluorophenyl)butyl bromide (13.66 g) in N,N-dimethylformamide (30 ml) over a period of 40 minutes. The mixture was stirred under a purging nitrogen atmosphere at room temperature for 3 days. The mixture was filtered through sintered glass and the filter pad washed with N,N-dimethylformamide. The filtrate and washings were evaporated at 30° under oil pump vacuum. The residual oil was extracted with ether and the extract was filtered. The solution was slurried with 200 g of silica gel for 20 minutes. The mixture was then filtered through a sintered glass filter. The silica gel was stirred repeatedly with fresh ether (10-15 times) until no more product was removed from the silica gel. The filtrate and washings were evaporated to an oil. To the oil dissolved in 2-propanol (125 ml) was added 75 ml of a saturated solution of etheral hydrogen chloride. The hydrochloride salt of the titled product crystallized slowly on standing at room temperature; wt. 18.8 g (76%), mp=211°-212°.

Workup

  1. filtrationThe mixture was filtered through sintered glass
  2. washthe filter pad washed with N,N-dimethylformamide
  3. customThe filtrate and washings were evaporated at 30° under oil pump vacuum
  4. extractionThe residual oil was extracted with ether
  5. filtrationthe extract was filtered
  6. waitThe solution was slurried with 200 g of silica gel for 20 minutes
  7. filtrationThe mixture was then filtered through a sintered glass
  8. filtrationfilter
  9. stirringThe silica gel was stirred repeatedly with fresh ether (10-15 times) until no more product
  10. customwas removed from the silica gel
  11. customThe filtrate and washings were evaporated to an oil
  12. dissolutionTo the oil dissolved in 2-propanol (125 ml)
  13. additionwas added 75 ml of a saturated solution of etheral hydrogen chloride
  14. customThe hydrochloride salt of the titled product crystallized slowly
  15. customon standing at room temperature

Sources & evidence

ORD record
ord-fcf578d3a8bb434ab40d59dbd1c6ecfe
Source dataset
uspto-grants-1989_01
Patent number
US04801706

Reaction notes

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