Sodium Hydroxide → HCID 10419502, compound

HRID 1646764Notes

Reaction equation

HRID 1646764 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][NH2:12].C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][CH2:11][NH2:12]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4397522-(1H-indol-2-yl)ethanamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10419502HCID 10419502, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(indol-2-yl)ethylamine (2.7 g) in acetic acid (25 ml) at 15° C. was added sodium cyanoborohydride (2.22 g) in one portion. The solution was stirred at room temperature for 15 hours and diluted with chilled water. The mixture was made basic with sodium hydroxide pellets and extracted three times with ether. The ether layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give 2-(2,3-dihydroindol-2-yl)ethylamine (1.41 g) as an oil. The oil was dissolved in tetrahydrofuran (50 ml) and treated with 1,1'-carboxyldiimidazole (1.13 g) at room temperature. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (30%-ethyl acetate-chloroform) to give crystals. The crystals were washed with ether to give 3,4,4a,5-tetrahydropyrimido[1,6-a]indol-1(2H)-one (0.74 g).

Workup

  1. extractionextracted three times with ether
  2. washThe ether layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b211c034747443d9c868114b0e907d5
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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