Benzoyl chloride → HCID 21313390, compound

HRID 2397483Notes

Reaction equation

HRID 2397483 reaction equation
[CH:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCCC(=O)CCCC.C(=O)([O-])[O-].[K+].[K+].C1(CC2CCCCN2CCCC(=O)CCCC)CCCCC1.COC1C=CC(NN)=CC=1.C1(CC2CCCCN2[CH2:75][CH2:76][C:77]2[C:85]3[C:80](=[CH:81][CH:82]=[C:83]([O:86][CH3:87])[CH:84]=3)[NH:79][C:78]=2[CH2:88][CH2:89][CH2:90][CH3:91])CCCCC1.[H-].[Na+].[Na].[C:95](Cl)(=[O:102])[C:96]1[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=1>C(O)C.CN(C=O)C>[C:95]([N:79]1[C:80]2[C:85](=[CH:84][C:83]([O:86][CH3:87])=[CH:82][CH:81]=2)[C:77]([CH2:76][CH2:75][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]2[CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[C:78]1[CH2:88][CH2:89][CH2:90][CH3:91])(=[O:102])[C:96]1[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=1

Participants

12

Reactant 9

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 77023(4-Methoxyphenyl)hydrazineHCID 4433338HCID 4433338, compoundHCID 5360545SodiumHCID 108990074-Octanone, 1-chloro-HCID 21313399HCID 21313399, compoundHCID 21313413HCID 21313413, compound

Product 1

HCID 21313390HCID 21313390, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

1-Benzoyl-3-[2-(2-cyclohexylmethylpiperidino)ethyl]-5-methoxy-2-butylindole is prepared by reaction of 2-cyclohexylmethylpiperidine with 1-chlorooctan-4-one in ethanol in the presence of anhydrous potassium carbonate; reaction of the resulting 1-(2-cyclohexylmethylpiperidino)octan-4-one with 4-methoxyphenylhydrazine in ethanol; and reaction of the resulting 3-[2-(2-cyclohexylmethylpiperidino)ethyl]-5-methoxy-2-butylindole with sodium hydride in DMF followed by reaction of the resulting sodium salt with benzoyl chloride all according to the procedure described above in Example 1.

Sources & evidence

ORD record
ord-bdacfe0b52424d5dafd47f68f6520661
Source dataset
uspto-grants-1977_05
Patent number
US04021431

Reaction notes

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