Acetone → HCID 57779501, compound

HRID 509196Notes

Reaction equation

HRID 509196 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Cl.Cl[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CN(C=O)C>[O:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=2)[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 57779489HCID 57779489, compound

Product 1

HCID 57779501HCID 57779501, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirring solution of compound 71 (1.5 g, 6.19 mmol), 4-(2-chloroethyl)morpholine hydrochloride (1.152 g, 6.19 mmol) and potassium carbonate (1.709 g, 12.38 mmol) in (1:1) DMF: acetone (60 mL) was heated to 60° C. for 16 h then concentrated. The crude residue was diluted with ethyl acetate and washed with water, dried over Na2SO4, filtered and concentrated to afford compound 73 (0.92 g, 42%) after purification by ISCO-HPLC (20 to 100% ethyl acetate in hexanes).

Workup

  1. concentrationthen concentrated
  2. additionThe crude residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e2270fbdd2d24e2ca7b989fac21304cb
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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