Methylparaben → Benzoic acid, 4-[(1-methyl-4-piperidinyl)oxy]-, methyl ester

HRID 1042431ノート

反応式

HRID 1042431 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:28][O:29][C:30](=[O:38])[C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:28][O:29][C:30](=[O:38])[C:31]1[CH:36]=[CH:35][C:34]([O:8][CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:33][CH:32]=1

参加物

6

反応物 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

HCID 18617571Benzoic acid, 4-[(1-methyl-4-piperidinyl)oxy]-, methyl ester収率 76.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1-methyl-piperidin-4-ol (6.8 g. 59 mmoles), PPh3 (triphenylphosphine, 15.5 g, 59 mmoles) and 4-hydroxy-benzoic acid methyl ester (6 g, 39 mmoles) in THF (150 ml) at 0° C., diethyl azodicarboxylate (9.5 ml, 59 mmoles) in THF (30 ml) was slowly added. The reaction mixture was allowed to warm to room temperature over a period of 24 hours. It was then evaporated and the residue redissolved in 5% aqueous citric acid (700 ml). The solution was washed with ethyl acetate (3×250 ml), made alkaline with concentrated NH4OH (pH ˜8) and then extracted with dichloromethane (3×250 ml). The combined dichloromethane extracts were washed with brine, dried and evaporated to give an oil which was purified by flash chromatography on silica gel using dichloromethane-MeOH (90:10) as eluent, to give the title compound as a yellow oil (7.4 g, 75%).

後処理

  1. customIt was then evaporated
  2. dissolutionthe residue redissolved in 5% aqueous citric acid (700 ml)
  3. washThe solution was washed with ethyl acetate (3×250 ml)
  4. extractionextracted with dichloromethane (3×250 ml)
  5. washThe combined dichloromethane extracts were washed with brine
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. customwas purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-b7f6b19492564896b19acd2d0e4ab892
出典データセット
uspto-grants-2013_10
特許番号
US08557857B2

反応ノート

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