Potassium Carbonate → HCID 10597140, compound

HRID 749402Notes

Reaction equation

HRID 749402 reaction equation
C1(S(Cl)(=O)=O)C2C(=CC=CC=2)C=CC=1.Cl[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[S:24]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25].[CH3:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C([O-])([O-])=O.[K+].[K+]>C(N(C(C)C)CC)(C)C.C(Cl)Cl.[I-].[Na+].CC#N>[CH3:37][CH:38]1[CH2:43][CH2:42][N:41]([CH2:16][CH2:17][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][N:19]2[S:24]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:40][CH2:39]1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 665601-Naphthalenesulfonyl chlorideHCID 693814-MethylpiperidineHCID 21717133HCID 21717133, compound

Product 1

HCID 10597140HCID 10597140, compound

Reagents, catalysts & solvents 4

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

The compound prepared as in Example 4 undergoes a substitution reaction with naphthalene-1-sulfonyl chloride (2 equiv) in diisopropylethylamine and CH2Cl2 to generate 2-(2-chloro-ethyl)-1-(naphthalene-1-sulfonyl)-piperidine. Displacement of the chloro substituent with 4-methylpiperidine with sodium iodide as catalyst in the presence of K2CO3 and CH3CN generates the title compound, a reported 5-HT7 receptor modulator (see, for example, Lovell, P. J., Bromidge, S. M., Dabbs, S., Duckworth, D. M., Forbes, I. T., Jennings, A. J., King, F. D., Middlemiss, D. N.; Rahman, S. K., Saunders, D. V., Collin, L. L., Hagan, J. J., Riley, G. J., Thomas, D. R., J. Med. Chem. 2000, 43, 342-345).

Workup

  1. customThe compound prepared as in Example 4

Sources & evidence

ORD record
ord-89483de23e364935842c6c9ac3a51d17
Source dataset
uspto-grants-2008_07
Patent number
US07402670B2

Reaction notes

Loading…