benzyl 2'-oxo-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-carboxylate → Spiro[piperidine-4,4'(1'H)-quinolin]-2'(3'H)-one

HRID 1695912Notes

Reaction equation

HRID 1695912 reaction equation
[O:1]=[C:2]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14](C(OCC3C=CC=CC=3)=O)[CH2:13][CH2:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1>CO.[Pd]>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]2([CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[CH2:11][C:2]1=[O:1]

Participants

4

Reactant 1

HCID 59433237benzyl 2'-oxo-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-carboxylate

Product 1

HCID 22380602Spiro[piperidine-4,4'(1'H)-quinolin]-2'(3'H)-oneYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of benzyl 2′-oxo-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1-carboxylate (1.2 g, 3.4 mmol) and Pd/C (200 mg) in MeOH (20 mL) was hydrogenated under atmosphere pressure at room temperature for 3 h. The catalyst was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC twice to give 1′H-spiro[piperidine-4,4′-quinolin]-2′(3′H)-one (110 mg, 11%) as a TFA salt. 1H NMR (CDCl3) δ 7.65 (d, J=7.5 Hz, 1H), 7.29-7.45 (m, 3H), 3.45 (d, J=12.3 Hz, 2H), 3.20 (t, J=12.3 Hz, 2H), 2.96 (s, 2H), 2.10-2.21 (m, 2H), 1.70 (d, J=14.1 Hz, 2H). MS (ESI) m/z 217.06 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC twice

Sources & evidence

ORD record
ord-e6e9b87891464abfbeb427b4f9000a2f
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

Loading…