Triethylamine → Hexahydro-1-[[4-(trifluoromethyl)phenyl]sulfonyl]-1H-1,4-diazepine

HRID 2289538Notes

Reaction equation

HRID 2289538 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:15]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68163Hexahydro-1,4-diazepineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 18698051Hexahydro-1-[[4-(trifluoromethyl)phenyl]sulfonyl]-1H-1,4-diazepineYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 1-(4-trifluoromethylphenylsulphonyl)homopiperazine was prepared as follows. 4-Trifluoromethylphenylsulphonylchloride (1.5 g) in 20 ml dichloromethane was added dropwise to 5 g homopiperazine and 1.8 ml triethylamine in 55 ml dichloromethane and left stirring overnight. Washed with water and brine, dried (MgSO4), and evaporated to give 1-(4-trifluoromethylphenylsulphonyl)homopiperazine (1.80 g) as a colourless solid; NMR (CDCl3) 1.75 (1H,br), 1.78-1.9 (2H,m), 2.9-3.0 (4H,m), 3.3-3.44 (4H,m), 7.78 (2H,d),

Workup

  1. customThe 1-(4-trifluoromethylphenylsulphonyl)homopiperazine was prepared
  2. waitleft
  3. washWashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1e8051e9fb714f51a407d13284e7964d
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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