Pyridine → HCID 9981372, compound

HRID 2227043Notes

Reaction equation

HRID 2227043 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([CH2:22][C:23](Cl)=[O:24])[CH:19]=[CH:20][CH:21]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH2:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][OH:31].N1C=CC=CC=1>O1CCCC1>[OH:31][CH2:30][C:29]1[CH:28]=[C:27]([NH:26][C:23](=[O:24])[CH2:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:17]=2)[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 802933-Aminobenzyl alcoholHCID 10090356HCID 10090356, compound

Product 1

HCID 9981372HCID 9981372, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10.5 g of 3-(tetradecyloxy)benzeneacetyl chloride in 110 ml of tetrahydrofuran is added a solution of m-aminobenzyl alcohol in 110 ml of tetrahydrofuran containing 9.05 g of pyridine followed by stirring at ambient temperature for 4 hours and storing in a refrigerator over the weekend. The solvent is evaporated and the residue is poured into water and extracted with tetrahydrofuran:ether. The organic layer is washed with dilute hydrochloric acid, dried and filtered through a pad of magnesium silicate. The filtrate is evaporated and the residue purified by high pressure liquid chromatography using 2:1 hexane:ethyl acetate to give 3.6 g of the desired product as a white powder, m.p. 108°-110° C. and 5.8 g of a white powder, m.p. 86°-90° C. found to be 3-(tetradecyloxy)-[3-[[[3-(tetradecyloxy)phenyl]acetyl]amino]phenyl]benzeneacetic acid methyl ester.

Workup

  1. customThe solvent is evaporated
  2. additionthe residue is poured into water
  3. extractionextracted with tetrahydrofuran
  4. washThe organic layer is washed with dilute hydrochloric acid
  5. customdried
  6. filtrationfiltered through a pad of magnesium silicate
  7. customThe filtrate is evaporated
  8. customthe residue purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-d1e120db563145eca10acbde5a4567cf
Source dataset
uspto-grants-1994_09
Patent number
US05350759

Reaction notes

Loading…