Benzoyl chloride → HCID 21313318, compound

HRID 971812Notes

Reaction equation

HRID 971812 reaction equation
C1(CC2CCCCN2CC[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22](OC)[CH:23]=3)[NH:18][CH:17]=2)CCCCC1.C1(CC2CCCCN2CCCC2C3C(=C(C(F)(F)F)C=CC=3)NC=2)CCCCC1.[CH:56]1([CH2:62][CH:63]2[CH2:68][CH2:67][CH2:66][CH2:65][N:64]2[CH2:69][CH2:70][CH2:71][CH2:72][C:73]2C3C(=C(C(F)(F)F)C=C(Cl)C=3)NC=2)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1.C1(CC2CCCCN2CCCC2C3C(=CC=C(OC)C=3)NC=2CO)CCCCC1.C1(CC2CCCCN2CCCC2C3C(=C(F)C=C(F)C=3)NC=2CO)CCCCC1.[H-].[Na+].[Na].C(Cl)(=O)C1C=CC=CC=1>CN(C=O)C>[CH:56]1([CH2:62][CH:63]2[CH2:68][CH2:67][CH2:66][CH2:65][N:64]2[CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1

Participants

10

Reactant 8

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 5360545SodiumHCID 21313384HCID 21313384, compoundHCID 21313401HCID 21313401, compoundHCID 21313404HCID 21313404, compoundHCID 21313412HCID 21313412, compoundHCID 21313421HCID 21313421, compound

Product 1

HCID 21313318HCID 21313318, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[2-(2-cyclohexylmethylpiperidino)ethyl]-5-methoxyindole (both disclosed U.S. Pat. No. 3,238,215); 3-[3-(2-cyclohexylmethylpiperidino)propyl]-7-trifluoromethylindole (m.p. 90.5°-91.5° C.); 3-[4-(2-cyclohexylmethylpiperidino)butyl]-5-chloro-7-trifluoromethylindole (m.p. 80°-81° C.) (both prepared according to the procedure described in U.S. Pat. No. 3,238,215); 3-[3-(2-cyclohexylmethylpiperidino)propyl]-5-methoxy-2-hydroxymethylindole; or 3-[3-(2-cyclohexylmethylpiperidino)propyl]-5,7-difluoro-2-hydroxymethylindole (both disclosed in U.S. Pat. No. 3,578,669) with a mineral oil dispersion of sodium hydride in DMF, and reaction of the resulting sodium salt with benzoyl chloride using the procedure described above in Example 1, affords the respective compounds of formula I in Examples 66-71 where, in each instance, A is benzoyl and N=B is 2-cyclohexylmethylpiperidino.

Workup

  1. customaffords the respective compounds of formula I in Examples 66-71 where

Sources & evidence

ORD record
ord-54044100323f476291feaf00800caf97
Source dataset
uspto-grants-1979_07
Patent number
US04160862

Reaction notes

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