2-Dimethylaminopyridine → 4-Methyl-1-piperidinecarboxylic acid 2-dibenzofuranyl ester

HRID 1492131Notes

Reaction equation

HRID 1492131 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.CN(C1C=CC=CN=1)C.[CH3:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31](Cl)=[O:32])[CH2:27][CH2:26]1>C1C=CC=CC=1>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:13]=[CH:14][C:2]=1[O:1][C:31]([N:28]1[CH2:29][CH2:30][CH:25]([CH3:24])[CH2:26][CH2:27]1)=[O:32]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 665872-DibenzofuranolHCID 152215164-Methylpiperidine-1-carbonyl Chloride

Product 1

HCID 98396324-Methyl-1-piperidinecarboxylic acid 2-dibenzofuranyl esterYield 104.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-hydroxydibenzofuran (10.0 g, 54.3 mmol), dimethylaminopyridine (DMAP) (7.3 g, 59.8 mmol) and 4-methyl-1-piperidinecarbonyl chloride (8.8 ml, 59.7 mmol) in 200 mL of benzene was refluxed under nitrogen for 7 hours. The reaction was extracted with 1N HCl and then the organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give 17.51 g of a light brown solid. Recrystallization of the solid from diisopropyl ether gave 10.82 g (64%) of the title compound as a light brown crystalline solid, mp 123°-125° C.

Workup

  1. temperaturewas refluxed under nitrogen for 7 hours
  2. extractionThe reaction was extracted with 1N HCl
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e658f3e0154c4613a787dec4c191a048
Source dataset
uspto-grants-1994_12
Patent number
US05373009

Reaction notes

Loading…