Hexahydro-1,4-diazepine → 1-[5-(Trifluoromethyl)pyridin-2-yl]-1,4-diazepane

HRID 1923482Notes

Reaction equation

HRID 1923482 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH:12]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 27607791-[5-(Trifluoromethyl)pyridin-2-yl]-1,4-diazepane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-5-trifluoromethylpyridine (362 mg, 1.99 mmol) and [1,4]-diazepane (1000 mg, 9.98 mmol) in DMF (6.0 mL) is stirred for 2 hours at room temperature followed by evaporation of the solvent DMF under vacuo. The residue is distributed between ethyl acetate (30 mL) and water (40 mL). The aqueous phase is extracted once with ethyl acetate (20 m) and the combined organic phases are dried with Na2SO4. Evaporation gives an oily residue (crude 1-(5-trifluoromethyl-pyridin-2-yl)-[1,4]-diazepane) which is used directly for reductive amination in the last step.

Workup

  1. customfollowed by evaporation of the solvent DMF under vacuo
  2. extractionThe aqueous phase is extracted once with ethyl acetate (20 m)
  3. dry with materialthe combined organic phases are dried with Na2SO4
  4. customEvaporation

Sources & evidence

ORD record
ord-85ab660f24094748a431a01a41def725
Source dataset
uspto-grants-2012_05
Patent number
US08178526B2

Reaction notes

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