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

HRID 1177094Notes

Reaction equation

HRID 1177094 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, 2 H) 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-c5d24b91da74432e9b8db5bfa39f0cf0
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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