2-Chloropyridine → 1-(PYRIDIN-2-YL)-1,4-DIAZEPANE

HRID 530460Notes

Reaction equation

HRID 530460 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[NH:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CC(N(C)C)=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:17]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 79772-ChloropyridineHCID 68163Hexahydro-1,4-diazepineHCID 81531Diisopropylethylamine

Product 1

HCID 27724021-(PYRIDIN-2-YL)-1,4-DIAZEPANEYield 72.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-Chloropyridine (3.00 g, 26.4 mmol), DIPEA (9.20 mL, 52.8 mmol) and homopiperazine (7.90 g, 79.3 mmol) were dissolved in DMA (10 mL) and heated using a microwave (180-200° C., absorption high) for 40 min. The reaction mixture was diluted with DCM (150 mL), washed with sat aq Na2CO3 (100 mL), brine (100 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (3.41 g, 72%) as a brown liquid. LCMS (ES+): 178.6 [MH]+.

Workup

  1. temperatureheated
  2. customa microwave (180-200° C., absorption high) for 40 min
  3. additionThe reaction mixture was diluted with DCM (150 mL)
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d2248bae6df4f3cad04ce8548b8b349
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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