Hexahydro-1,4-diazepine → 1-(1,3-thiazol-2-yl)-1,4-diazepane

HRID 530453Notes

Reaction equation

HRID 530453 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1>CC(N(C)C)=O>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[N:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 764302-Bromothiazole

Product 1

HCID 167832631-(1,3-thiazol-2-yl)-1,4-diazepaneYield 94%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-Bromothiazole (1.00 g, 6.10 mmol) and homopiperazine (2.44 g, 24.4 mmol) were dissolved in DMA (1 mL) and heated using a microwave (180° C., absorption high) for 30 min. The reaction mixture was dissolved in DCM (50 mL), washed with sat aq Na2CO3 (50 mL), brine (50 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound (1.05 g, 94%) as a yellow solid. LCMS (ES+): 184.2 [MH]+.

Workup

  1. temperatureheated
  2. customa microwave (180° C., absorption high) for 30 min
  3. dissolutionThe reaction mixture was dissolved in DCM (50 mL)
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22db9018bb234df2b1ed8981ddabba62
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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