N-(3-methoxyphenyl)piperazine → HCID 69605056, compound

HRID 860002Notes

Reaction equation

HRID 860002 reaction equation
BrC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH:33]=[CH:34][CH:35]=1>CS(C)=O.C(=O)(O)[O-].[Na+]>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([N:36]2[CH2:41][CH2:40][N:39]([CH2:12][C@@H:13]3[O:27][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]5)[CH2:38][CH2:37]2)[CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 81430N-(3-methoxyphenyl)piperazineHCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate

Product 1

HCID 69605056HCID 69605056, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (702 mg, 1.56 mmol) and 3-methoxyphenyl piperazine (890 mg, 4.63 mmol) in anhydrous DMSO (10 mL) were heated at 65° C. overnight. The cooled reaction mixture was diluted with saturated aqueous sodium bicarbonate (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography on silica gel (50% EtOAc/hexanes) afforded 560 mg (88%) of the desired product as a white solid: mp 90–91° C.; MS (ESI) m/z 406 [M+H]+.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a9b32642ae045f586f73d7964a9b486
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

Loading…