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Diphenylacetic Acid → 1-[4-(2-Hydroxyethyl)piperidin-1-yl]-2,2-diphenylethanone

HRID 2370933
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2370933
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.[C:32]1([CH:38]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:39](O)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[OH:9][CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:39](=[O:40])[CH:38]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:2][CH2:3]1
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Komponenten

7

Edukt 5

HCID 8333Diphenylacetic AcidHCID 739534-PiperidineethanolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 58230382
1-[4-(2-Hydroxyethyl)piperidin-1-yl]-2,2-diphenylethanone
Ausbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Piperidin-4-ylethanol (1.12 g; 8.65 mmol) was introduced into dimethylformamide (DMF, 10 ml). Then hydroxybenzotriazole (HOBT, 1.46 g, 9.51 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl, 1.83 g; 9.51 mmol) and diphenylacetic acid (2.02 g; 9.51 mmol) were added in this sequence. N,N-diisopropyl-ethylamine (DIEA; 1.67 ml; 9.51 mmol) was then added to the reaction mixture, which was stirred at RT for 16 h. The reaction solution was concentrated under reduced pressure. The residue was taken up in EA, and the organic solution was washed successively with saturated NaHCO3 solution, 2N HCl and saturated NaCl solution. The organic phase was separated off, dried over Na2SO4, filtered and concentrated. The 1-[4-(2-hydroxyethyl)piperidin-1-yl]-2,2-diphenylethanone (2.39 g; 8.11 mmol) obtained in this way was reacted further without further purification.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washthe organic solution was washed successively with saturated NaHCO3 solution, 2N HCl and saturated NaCl solution
  3. customThe organic phase was separated off
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2c26a5279917433da13214da87378506
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710232B2

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