Triethylamine → HCID 58266829, compound

HRID 1888407Notes

Reaction equation

HRID 1888407 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C([N:12]([CH2:15][CH3:16])[CH2:13]C)C.N1CCC1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:12]2[CH2:13][CH2:16][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10422AzetidineHCID 685274-Bromobenzyl bromide

Product 1

HCID 58266829HCID 58266829, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromobenzyl bromide (1.00 g, 4.0 mmol) and triethylamine (0.84 ml, 6.0 mmol) in THF (20 mL) was stirred at ambient temperature for 10 minutes. Azetidine (0.54 ml, 8.0 mmol) was then added and a white precipitate resulted. The slurry was stirred at ambient temperature for 18 h then evaporated in vacuo. The resultant residue was partitioned between DCM and saturated aqueous sodium hydrogen carbonate, the organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (0.76 g, 3.40 mmol) as a colourless oil. 1H NMR (CDCl3, 400 MHz): 7.42 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.2 Hz, 2H), 3.50 (s, 2H), 3.19 (t, J=7.0 Hz, 4H), 2.08 (p, J=7.0 Hz, 2H).

Workup

  1. customa white precipitate resulted
  2. customthen evaporated in vacuo
  3. customThe resultant residue was partitioned between DCM and saturated aqueous sodium hydrogen carbonate
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6acaa6053b604d24a46327139d952270
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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