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

HRID 2370933Notes

Reaction equation

HRID 2370933 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 582303821-[4-(2-Hydroxyethyl)piperidin-1-yl]-2,2-diphenylethanoneYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2c26a5279917433da13214da87378506
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

Loading…