Benzylamine → HCID 15288858, compound

HRID 1613462Notes

Reaction equation

HRID 1613462 reaction equation
ClCC([O:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH3:15])[C:10]3[C:16](=O)[CH2:17][CH2:18][C:9]=3[C:8]=2[CH:7]=1)=O.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH3:15][N:11]1[C:12]2[CH:13]=[CH:14][C:6]([OH:5])=[CH:7][C:8]=2[C:9]2[CH2:18][CH2:17][C:16](=[N:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]1=2

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 19003099HCID 19003099, compound

Product 1

HCID 15288858HCID 15288858, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of 7-chloroacetyloxy-1,4-dihydro-4-methycyclopent[b]-indol-3(2H)-one (6.0 g) in toluene (50 ml) was added benzylamine (9.2 g) and the mixture was heated at reflux temperature with azeotropic removal of water using a Dean Stark trap. After 4 hours, TLC analysis indicated complete conversion to product. The mixture was allowed to cool to room temperature and filtered, and the solid material was washed with acetonitrile. The filtrate and washings were combined, concentrated and purified by flash chromatography on silica gel (2:1 hexane/acetone as eluent). The crystals which formed in the product-containing fractions were collected via filtration to give 4-methyl-3-phenylmethylimino-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol (1.1 grams) and the filtrate was concentrated to give an oil (3.0 grams) which crystallized upon standing.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature
  3. customwith azeotropic removal of water using a Dean Stark trap
  4. filtrationfiltered
  5. washthe solid material was washed with acetonitrile
  6. concentrationconcentrated
  7. custompurified by flash chromatography on silica gel (2:1 hexane/acetone as eluent)
  8. customThe crystals which formed in the product-containing fractions
  9. filtrationwere collected via filtration

Sources & evidence

ORD record
ord-a01a907460154e7793249bbc23231f1b
Source dataset
uspto-grants-1993_03
Patent number
US05192789

Reaction notes

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