Piperidine → HCID 68871600, compound

HRID 2105839Notes

Reaction equation

HRID 2105839 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[I:13])[C:7]([OH:9])=O)[CH3:2].C(Cl)(=O)C(Cl)=O.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl.CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:9])[CH:10]=[CH:11][C:12]=1[I:13])[CH3:2]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 65578Oxalyl chlorideHCID 53442006HCID 53442006, compound

Product 1

HCID 68871600HCID 68871600, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3-Ethoxy-4-iodo-benzoic acid (2.73 grams, 9.36 mmol) was suspended in methylene chloride (25 mL), and oxalyl chloride (5.15 mL, 2.0 M in methylene chloride, 10.3 mmol) was added by pipette. Three drops of dimethylformamide was added and this mixture was stirred overnight at room temperature. The volatiles from the now homogeneous reaction were removed under vacuum and the residue reconstituted in methylene chloride. One half of this was treated with piperidine (2.0 mL, 20 mmol). The mixture was stirred at room temperature for 2 h. The reaction was diluted with methylene chloride, washed with 1.0 M hydrochloric acid, water, saturated sodium bicarbonate solution and brine. The organic layers was dried (magnesium sulfate), filtered and concentrated to give (3-ethoxy-4-iodo-phenyl)-piperidin-1-yl-methanone (1.69 g, 100%).

Workup

  1. customThe volatiles from the now homogeneous reaction
  2. customwere removed under vacuum
  3. stirringThe mixture was stirred at room temperature for 2 h
  4. washwashed with 1.0 M hydrochloric acid, water, saturated sodium bicarbonate solution and brine
  5. dry with materialThe organic layers was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2a651f7fbc50486db8c439500f85c684
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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