Benzoyl chloride → HCID 21313407, compound

HRID 2397496Notes

Reaction equation

HRID 2397496 reaction equation
ClCCC1C2C(=CC(OC)=C(OC)C=2)NC=1C(OCC)=O.C1(CC2CCCCN2)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+].[CH:41]1([CH2:47][CH:48]2[CH2:53][CH2:52][CH2:51][CH2:50][N:49]2[CH2:54][CH2:55][C:56]2[C:64]3[C:59](=[CH:60][C:61]([O:67][CH3:68])=[C:62]([O:65][CH3:66])[CH:63]=3)[NH:58][C:57]=2[C:69]([O:71][CH2:72][CH3:73])=[O:70])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.[H-].[Na+].[Na].[C:77](Cl)(=[O:84])[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1>CN(C=O)C.CC(C)=O>[C:77]([N:58]1[C:59]2[C:64](=[CH:63][C:62]([O:65][CH3:66])=[C:61]([O:67][CH3:68])[CH:60]=2)[C:56]([CH2:55][CH2:54][N:49]2[CH2:50][CH2:51][CH2:52][CH2:53][CH:48]2[CH2:47][CH:41]2[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]2)=[C:57]1[C:69]([O:71][CH2:72][CH3:73])=[O:70])(=[O:84])[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1

Participants

10

Reactant 7

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 4433338HCID 4433338, compoundHCID 5360545SodiumHCID 21313308HCID 21313308, compoundHCID 21313344Ethyl 3-(2-chloroethyl)-5,6-dimethoxy-1H-indole-2-carboxylate

Product 1

HCID 21313407HCID 21313407, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Reaction of 3-(2-chloroethyl)-5,6-dimethoxy-2-carbethoxyindole (U.S. Pat. No. 3,562,278) with 2-cyclohexylmethylpiperidine in refluxing acetone in the presence of sodium carbonate and reaction of the resulting 3-[2-(2-cyclohexylmethylpiperidino)ethyl]5,6-dimethoxy-2-carbethoxyindole with sodium hydride in DMF followed by reaction of the resulting sodium salt with benzoyl chloride affords 1-benzoyl-3-[2-(2-cyclohexylmethylpiperidino)ethyl]-5,6-dimethoxy-2-carbethoxyindole.

Sources & evidence

ORD record
ord-bfce0ac8d0e2438581a210f1d3900765
Source dataset
uspto-grants-1977_05
Patent number
US04021431

Reaction notes

Loading…