Acetic Acid → 3-Piperidin-3-ylpropan-1-ol

HRID 2045692ノート

反応式

HRID 2045692 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH:2]=1.CC(O)=O.Cl.CCO>O.[Pt](=O)=O.O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:2]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 702EthanolHCID 178613-Pyridinepropanol

生成物 1

HCID 47124763-Piperidin-3-ylpropan-1-ol

試薬・触媒・溶媒 2

HCID 11139377Platinum dioxide monohydrate触媒HCID 962Water溶媒

実験手順

A 500 mL Parr hydrogenation bottle was charged with 3-Pyridinepropanol (10.0 g, 72.9 mmol), platinum(IV)oxide hydrate (Adam's Catalyst) (500 mg), AcOH (30 mL), and HCl, 37% (1 mL). Contents of the bottle were hydrogenated at 47 psi for three days. EtOH and water were added, and the reaction mixture was filtered through CELITE. NaOH (10 N) was added and the mixture was extracted with methylene chloride, dried with anhydrous MgSO4, filtered and concentrated. The product was concentrated from PhMe and used without further purification. 1H NMR (CD3OD): δ 3.55 (t, J=5 Hz, 2H), 3.0{tilde over (5)} 2.95 (m, 2H), 2.5{tilde over (5)} 2.45 (m, 1H), 2.23 (t, J=10 Hz, 1H), 1.8 9 1.86 (m, 1H), 1.7{tilde over (0)} 1.66 (m, 1H), 1.6 0 1.44 (m, 4H), 1.2{tilde over (8)} 1.22 (m, 2H), 1.0 6 1.00 (m, 1H) ppm.

後処理

  1. filtrationthe reaction mixture was filtered through CELITE
  2. additionNaOH (10 N) was added
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialdried with anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe product was concentrated from PhMe
  8. customused without further purification

出典と根拠

ORDレコード
ord-e4a8139c66f045edb010d4c57cc3fb25
出典データセット
uspto-grants-2013_11
特許番号
US08591878B2

反応ノート

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