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

HRID 2292277Notes

Reaction equation

HRID 2292277 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH2:11]Br)=[CH:4][CH:3]=1.[C:20]([N:28]1[CH:34]=[CH:33][N:32]=[CH:31][CH2:30][N:29]1[C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>CCOCC>[C:20]([N:28]1[CH2:34][CH2:33][N:32]([CH2:11][CH2:10][CH2:9][CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:31][CH2:30][N:29]1[C:35](=[O:42])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 937631,1'-(4-Bromobutylidene)bis[4-fluorobenzene]HCID 212772311,2-dibenzoyl-1H-1,2,5-triazepine

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4,4-bis(4-fluorophenyl)butyl bromide (2.08 g), 1,2-dibenzoyl-1H-1,2,5-triazepine (2.0 g), powdered anhydrous sodium carbonate (2.71 g) and N,N-dimethylformamide (20 ml, dried over 4A molecular sieves) was stirred at room temperature under a nitrogen atmosphere for three days. The mixture was filtered and the filtrate was evaporated under oil pump vacuum to an oil. The oil was chromatographed on a column of silica gel; elution with ethyl acetate-dichloromethane (2:3) giving a major product. The hydrochloride salt of the titled compound was formed in ether from this material; wt. 2.0 g (52%), mp=216°-218°.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated under oil pump vacuum to an oil
  3. customThe oil was chromatographed on a column of silica gel
  4. washelution with ethyl acetate-dichloromethane (2:3)
  5. customgiving a major product

Sources & evidence

ORD record
ord-364d0c76dbe5453f83ccb691db5a60c2
Source dataset
uspto-grants-1989_01
Patent number
US04801706

Reaction notes

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