Triethylamine → HCID 16894675, compound

HRID 1404446Notes

Reaction equation

HRID 1404446 reaction equation
[C:1]1([CH:7]2[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19](Cl)=[O:20].C(N(CC)CC)C>ClCCl>[C:1]1([CH:7]2[O:12][CH2:11][CH2:10][N:9]([C:19](=[O:20])[CH2:18][C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 911012-PhenylmorpholineHCID 1623622-Thiopheneacetyl chloride

Product 1

HCID 16894675HCID 16894675, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-phenylmorpholine (326 mg, 2 mmol) in dry dichloromethane (6 mL) is cooled in an ice bath, and thiophen-2-yl-acetyl chloride (401.5 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 1:3). The fractions containing 1-(2-phenylmorpholin-4-yl)-2-(thiophen-2-yl)ethan-1-one are collected and the solvent is removed in vacuo to give 511 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 1:3)
  5. additionThe fractions containing 1-(2-phenylmorpholin-4-yl)-2-(thiophen-2-yl)ethan-1-one
  6. customare collected
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c3eba62e6ddd48e2a6d7a3d7c9985b6b
Source dataset
uspto-grants-2014_12
Patent number
US08912329B2

Reaction notes

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