1'-benzylspiro[indoline-3,4'-piperidin]-2-one synthesis
- Product Name:1'-benzylspiro[indoline-3,4'-piperidin]-2-one
- CAS Number:1086063-19-5
- Molecular formula:C19H20N2O
- Molecular Weight:292.37
Yield:1086063-19-5 73%
Reaction Conditions:
Stage #1: 2-oxoindolewith sodium hexamethyldisilazane in tetrahydrofuran at -78; for 0.5 h;
Stage #2: N-benzyl-2-chloro-N-(2-chloroethyl)ethanamine hydrochloride in tetrahydrofuran; for 15 h;
Steps:
3.1
Example 3Preparation of Compound 3 NaHMDS 1 M in THF (50 mL, 50 mmol) was added to a stirred solution of 1,3-dihydro-2H-indol-2-one 3a (1.33 g, 10 mmol) in dry THF (20 mL) at -78° C. and the mixture was stirred for 30 minutes. Then N-Benzyl-N,N-bis(2-chloroethyl)amine hydrochloride (2.68 g, 15 mmol, 1.5 eq) was added and the resulting mixture was stirred for 15 hours and slowly warmed to room temperature. The mixture was diluted with dichloromethane, then water. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified using column chromatography (dichloromethane:MeOH 95:5) to provide compound 3b (1.7 g, 73%).
References:
US2011/166124,2011,A1 Location in patent:Page/Page column 28-29
