N,N,N',N'-Tetramethylazodicarboxamide → HCID 53778444, compound

HRID 843164Notes

Reaction equation

HRID 843164 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].O[CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(P(CCCC)CCCC)CCC.N(C(N(C)C)=O)=NC(N(C)C)=O>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 79341Piperidin-4-olHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 53778444HCID 53778444, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (100 mg), 4-hydroxypiperidine (46 mg), tributylphosphine (170 μl) and 1,1′-azobis(N,N-dimethylformamide) (120 mg) in benzene (2 ml) was heated at 60° C. for one hour. The suspension was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was separated by silica gel column chromatography developed by dichloromethane-methanol to give 3-methyl-4-(piperidin-4-yloxy)-benzofuran-2-carboxylic acid ethyl ester (24 mg) as a colorless oil.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-030024d306624439a7a142e45cfe9ce1
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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