Triethylamine → HCID 47082883, compound

HRID 1404459Notes

Reaction equation

HRID 1404459 reaction equation
[CH2:1]([CH:8]1[CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]1([CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([CH:8]1[CH2:9][N:10]([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117898654-Phenylbutanoyl ChlorideHCID 162278383-Benzylazetidine

Product 1

HCID 47082883HCID 47082883, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-benzylazetidine (294 mg, 2 mmol) in dry dichloromethane (6 mL) is cooled in an ice bath, and 4-phenylbutyryl chloride (456.6 mg, 2.5 mmol, 1.25 eq) and triethylamine (417 μL, 3 mmol, 1.5 eq) are added. After stirring for 6 hours at room temperature the reaction mixture is diluted with dichloromethane (10 mL). The organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine. After drying over Na2SO4, dichloromethane is removed in vacuo and the crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:5). The fractions containing 1-(3-benzylazetidin-1-yl)-4-phenylbutan-1-one are collected and the solvent is removed in vacuo to give 479 mg of colorless oil.

Workup

  1. washThe organic solution is subsequently washed with 1 M KHSO4, 5% NaHCO3 and brine
  2. dry with materialAfter drying over Na2SO4, dichloromethane
  3. customis removed in vacuo
  4. customthe crude material is purified by flash chromatography (silicagel, ethyl acetate/toluene 1:5)
  5. additionThe fractions containing 1-(3-benzylazetidin-1-yl)-4-phenylbutan-1-one
  6. customare collected
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a4eb278df9ad4291a6b33086f771953e
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

Loading…