Morpholine → HCID 59419876, compound

HRID 2189968Notes

Reaction equation

HRID 2189968 reaction equation
C(O[C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][CH2:16][C:17]2=[O:20])=[CH:12][CH:11]=1)=[O:5])C.C(N(CC)C(C)C)(C)C.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(Cl)Cl>[N:30]1([C:4](=[O:5])[CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH2:16][C:17]3=[O:20])=[CH:12][CH:11]=2)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 59419872HCID 59419872, compound

Product 1

HCID 59419876HCID 59419876, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-(3-ethoxycarbonylpropoxy)-1-tetralone (0.925 g, 3.7 mmol), HUBT (1.415 g, 3.7 mmol), N,N-diisopropylethyl amine (1.3 mL) in CH2Cl2 (20 mL) was added morpholine (0.330 mL, 3.7 mmol) at room temperature and under argon atmosphere. The reaction mixture was then stirred at room temperature for 24 h and then concentrated. The residue dissolved in ethyl acetate (50 mL) and the organic layer was washed with dil. HCl, water, brine, and dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified on the column of silica gel using ethyl acetate-hexane (8:2) as an eluent to give 7-(4-morpholin-4-yl-4-oxo-butoxy)-1-tetralone (1.010 g, 86%): mp 88-90° C., 1H NMR (500 MHz, CDCl3): δ 2.07-2.15 (m, 4H), 2.50 (t, J=7.5 Hz, 2H), 2.61 (T, J=7.5 Hz, 2H), 2.88 (t, J=6.0 Hz, 2H), 3.46 (t, J=5.0 Hz, 2H), 3.59-3.66 (m, 6H), 4.04 (t, J=6.0 Hz, 2H), 7.01-7.03 (dd, J=3.0 and 8.5 Hz, 1H), 7.15 (d, J=8.5 Hz, 1H), 7.48 (d, J=3.0 Hz, 1H). HFABMS m/z 318.1706 (calc for C18H23NO4, MH+, 318.1705).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue dissolved in ethyl acetate (50 mL)
  3. washthe organic layer was washed with dil. HCl, water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on the column of silica gel

Sources & evidence

ORD record
ord-5ccfb619e1b74670b9dcb5cbb6d1a007
Source dataset
uspto-grants-2012_12
Patent number
US08324262B2

Reaction notes

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