Diethyl Ether → 4-Benzoyl-1-(5,6-dimethoxy-2-methylindol-3-ylglyoxyloyl)piperidine

HRID 867026

Reaction equation

HRID 867026 reaction equation
CCOCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[NH:13][C:12]([CH3:19])=[C:11]2[C:20](=[O:24])[C:21](Cl)=[O:22].[C:25]([CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.O>[C:25]([CH:33]1[CH2:38][CH2:37][N:36]([C:21](=[O:22])[C:20]([C:11]2[C:10]3[C:14](=[CH:15][C:16]([O:17][CH3:18])=[C:8]([O:7][CH3:6])[CH:9]=3)[NH:13][C:12]=2[CH3:19])=[O:24])[CH2:35][CH2:34]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 226102Phenyl(piperidin-4-yl)methanoneHCID 131955395,6-Dimethoxy-2-methyl-3-indoleglyoxylyl chloride

Product 1

HCID 131955404-Benzoyl-1-(5,6-dimethoxy-2-methylindol-3-ylglyoxyloyl)piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The above ether suspension of 5,6-dimethoxy-2-methyl-3-indoleglyoxylyl chloride is added portionwise to a cooled stirring mixture of 4-benzoylpiperidine [Example 9(a)], 150 ml of water, 150 ml of chloroform and 25 g of potassium carbonate. The mixture is stirred for 16 hours at ambient temperature, the organic layer is separated and the solvent is removed, leaving a brown oil which is triturated with cyclohexane and then stirred for 16 hours with ether. A white solid results which is collected, dried and recrystallized thrice from methanol to give the compound, mp 188°-190° C., 4-benzoyl-1-(5,6-dimethoxy-2-methylindol-3-ylglyoxyloyl)piperidine.

Workup

  1. additionis added portionwise to a cooled
  2. stirringThe mixture is stirred for 16 hours at ambient temperature
  3. customthe organic layer is separated
  4. customthe solvent is removed
  5. customleaving a brown oil which
  6. customis triturated with cyclohexane
  7. stirringstirred for 16 hours with ether
  8. customA white solid results which
  9. customis collected
  10. customdried
  11. customrecrystallized thrice from methanol

Sources & evidence

ORD record
ord-b08f444901ae49b4bd339ed9754cb66e
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Linked notes

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