5-Benzyloxyindole → HCID 12229248, compound

HRID 1766220Notes

Reaction equation

HRID 1766220 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:20][N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1>CO>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:24]1[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH:23]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 146245-BenzyloxyindoleHCID 14797Potassium HydroxideHCID 740491-Methyl-4-piperidone

Product 1

HCID 12229248HCID 12229248, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of potassium hydroxide (22 g, 392 mmol) in methanol (160 mL) was added 5-benzyloxyindole (24.7 g, 111 mmol) followed by 1-methyl-4-piperidone (17.7 mL, 144 mmol) and methanol (80 mL). The reaction mixture was stirred at reflux for 18 h, cooled to ambient temperature and filtered. The precipitate was washed with methanol and dried under vacuum to give 31.7 g (90%) of the title compound: mp=197-199° C. dec; MS(m/e): 318 (M+). Calculated for C21H22N2O: C, 79.21; H, 6.96; N, 8.80. Found: C, 79.24; H, 6.99; N, 8.85.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationfiltered
  3. washThe precipitate was washed with methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f92b7e95d75f46dca27dace9711e07be
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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