Triethylamine → Azetidin-1-yl-(2,4-difluorophenyl)methanone

HRID 1643568Notes

Reaction equation

HRID 1643568 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[NH:13]1[CH2:16][CH2:15][CH2:14]1.CCN(CC)CC>C(Cl)Cl>[N:13]1([C:4]([C:3]2[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:2]=2[F:1])=[O:5])[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5880812,4-Difluorobenzoyl chlorideHCID 12308726Azetidine hydrochloride

Product 1

HCID 59560289Azetidin-1-yl-(2,4-difluorophenyl)methanoneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-difluorobenzoyl chloride (1.14 g, 6.46 mmol) in CH2Cl2 was added azetidine hydrochloride (1.46 g, 15.6 mmol) and Et3N (2.70 mL, 19.4 mmol). The reaction mixture was stirred at room temperature for 1 hr, quenched with H2O (100 mL), and extracted with CH2Cl2 (2×100 mL). The organic layers were dried over MgSO4 and concentrated to give an off-white solid (896 mg, 76% yield) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.52-7.59 (m, 1 H) 6.91-6.98 (m, 1 H) 6.81-6.87 (m, 1 H) 4.21 (t, J=7.71 Hz, 2 H) 4.11 (t, J=7.71 Hz, 2H) 2.30-2.38 (m, 2 H).

Workup

  1. customquenched with H2O (100 mL)
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f94feaaffbc54c639272651a5dd5440b
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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