Cesium carbonate → HCID 68499165, compound

HRID 1176283Notes

Reaction equation

HRID 1176283 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH:9]2[O:24][CH2:25][C:26]2[CH:35]=[C:34]3[C:29]([CH2:30][CH2:31][C:32](=[O:41])[N:33]3[CH2:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:28][CH:27]=2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O[CH2:52][CH2:53][CH2:54][O:55][CH:56]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH3:57])(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:40][O:39][CH2:38][CH2:37][CH2:36][N:33]1[C:34]2[C:29](=[CH:28][CH:27]=[C:26]([CH2:25][O:24][CH:9]3[CH:8]([C:5]4[CH:6]=[CH:7][C:2]([O:1][CH2:52][CH2:53][CH2:54][O:55][CH:56]([C:58]5[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=5)[CH3:57])=[CH:3][CH:4]=4)[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[O:15])[CH2:10]3)[CH:35]=2)[CH2:30][CH2:31][C:32]1=[O:41]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68502032HCID 68502032, compoundHCID 86609991HCID 86609991, compound

Product 1

HCID 68499165HCID 68499165, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 0.200 g of benzyl 4-(4-hydroxyphenyl)-3-[1-(3-methoxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-ylmethoxy]piperidine-1-carboxylate, 0.157 g of 3-(1-phenylethoxy)propyl toluene-4-sulphonate and 0.173 g of caesium carbonate in 2.5 ml of acetonitrile is stirred at 80° C. over 2 hours. The reaction mixture is subsequently cooled, poured onto water (25 ml) and extracted with tert-butyl methyl ether (2×25 ml). The organic phases are washed with brine (1×25 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.19 (2:1 EtOAc-heptane); Rt=6.03.

Workup

  1. temperatureThe reaction mixture is subsequently cooled
  2. additionpoured onto water (25 ml)
  3. extractionextracted with tert-butyl methyl ether (2×25 ml)
  4. washThe organic phases are washed with brine (1×25 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fc59702ed2df419a8e229aa4479042c2
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

Loading…