Reaction #90514

Reaction equation

p-Toluene sulphonic acid

13

6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

1-benzylpiperidine-4-carbaldehyde

→

(E)-2-((1-benzylpiperidin-4-yl)methylene)-6-methoxy-5-morpholino-2, 3-dihydro-1H-inden-1-one

Solvents

ethyl acetate

toluene

Conditions

Workup

1. 1
   Washwashed with water (3×25 mL)
2. 2
   DryingThe organic layer was dried over sodium sulphate
3. 3
   Concentrationconcentrated
4. 4
   Otherto get the crude material, which
5. 5
   Otherwas purified through flash chromatography
6. 6
   WashEluting at 30% ethyl acetate in hexane

Procedure

To a solution of 13 (150 mg, 0.607 mmol) in toluene 15 mL was added 1-benzylpiperidine-4-carbaldehyde 21 (123.4 mg, 0.607 mmol). p-Toluene sulphonic acid (PTSA) (230.9 mg, 1.214 mmol) was added to the reaction mixture, and stirred at 120° C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude material, which was purified through flash chromatography using 100-200 mesh silica gel. Eluting at 30% ethyl acetate in hexane gave yellow coloured solid (E)-2-((1-benzylpiperidin-4-yl)methylene)-6-methoxy-5-morpholino-2, 3-dihydro-1H-inden-1-one 22.

Source