Cesium carbonate → HCID 10626061, compound

HRID 1421393Notes

Reaction equation

HRID 1421393 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[N:20]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:21](=[O:23])[CH3:22])=[CH:5][CH:4]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.CO.C(Cl)(Cl)Cl>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[N:20]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)=[CH:28][CH:29]=2)[C:21](=[O:23])[CH3:22])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 10693387HCID 10693387, compoundHCID 21584188Chloroform methanol

Product 1

HCID 10626061HCID 10626061, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-methoxyphenyl)-3-[N-(4-hydroxyphenyl)acetamido]-6-methoxy-benzo[b]thiophene (1.31 g, 3.13 mmol) and Cs2CO3 (4.10 g, 12.50 mmol) in 15 mL of anhydrous DMF was added 2-chlorethylpiperidine hydrochloride (1.15 g, 6.26 mmol). The resulting mixture was stirred vigorously at room temperature for 5 h. The reaction mixture was diluted with 200 mL of H2O, and then extracted several times with EtOAc. The combined organic was then washed with H2O several times and then dried (Na2SO4), Concentration in vacuo provided an oil. Chromatography (1% CH3OH/CHCl3, SiO2) provided 1.49 g (90%) of 2-(4-methoxyphenyl-3-[N-[4-[2-(1-piperidinyl)ethoxy]phenyl]acetamido]-6-methoxybenzo[b]thiophene as an amber oil. 1H NMR (DMSO-d6) δ (doubling due to amide rotamers) 7.66-6.70 (m, 11 H), 3.93 (m, 2H) 3.78 and 3.58 (s, 6H), 2.8-2.30 (m, 6H), 2.01 and 1.78 (s, 3H), 1.52-1.11 (m, 6H). FD mass spec: 530. Anal. Calcd. for C31H34N2O4S: C, 70.16; H, 6.46; N, 5.28. Found: C, 70.33; H, 6.34; N, 5.35.

Workup

  1. extractionextracted several times with EtOAc
  2. washThe combined organic was then washed with H2O several times
  3. customdried
  4. concentration(Na2SO4), Concentration in vacuo
  5. customprovided an oil

Sources & evidence

ORD record
ord-4b5b7c32404547fca3ac957c5b6b4cfc
Source dataset
uspto-grants-2000_06
Patent number
US06075151

Reaction notes

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