1-Methyl-4-piperidone → HCID 10180234, compound

HRID 2212825Notes

Reaction equation

HRID 2212825 reaction equation
C[O-].[Na+].[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][S:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[CH3:27][N:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1>CO>[CH3:27][N:28]1[CH2:29][CH:30]=[C:31]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[C:9]([NH:13][S:14]([C:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:20]=[CH:19][CH:18]=4)(=[O:15])=[O:16])[CH:8]=3)[NH:4][CH:5]=2)[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 740491-Methyl-4-piperidoneHCID 3408346HCID 3408346, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10180234HCID 10180234, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 712 mg (13.2 mMol) of sodium methoxide in 100 ml of methanol are added 850 mg (264 mMol) of N-[1H-indol-5-yl]naphthalene-1-sulphonamide followed by 596 mg (5.28 mMol) of 1-methyl-4-piperidone and the resulting solution is heated to reflux for 48 hours. The reaction mixture is concentrated at reduced pressure and the residue obtained is purified by chromatography over silica gel, using as eluent mixtures of methylene chloride/methanol/ammonia, to yield 573 mg (52%) of N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide as a solid with m.p.=244-245° C.

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureto reflux for 48 hours
  3. concentrationThe reaction mixture is concentrated at reduced pressure
  4. customthe residue obtained
  5. customis purified by chromatography over silica gel

Sources & evidence

ORD record
ord-e74cb26397b94b58af25d2a0fd93ddb0
Source dataset
uspto-grants-2006_09
Patent number
US07105515B2

Reaction notes

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