Sodium Carbonate → 2,3-Dihydro-6-(2-dimethylaminoethoxy)-5-methoxy-1H-indole

HRID 1419825Notes

Reaction equation

HRID 1419825 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][C:7]=1[O:15][CH3:16].C([BH3-])#N.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.O>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][NH:12]2)=[CH:8][C:7]=1[O:15][CH3:16]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 105376592-((5-Methoxy-1H-indol-6-yl)oxy)-N,N-dimethylethan-1-amine

Product 1

HCID 104899992,3-Dihydro-6-(2-dimethylaminoethoxy)-5-methoxy-1H-indoleYield 74.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A stirred solution of 6-(2-dimethylaminoethoxy)-5-methoxy-1H-indole (D16, 0.50 g, 2.1 mmole) in glacial acetic acid (10 ml) at room temperature was treated portionwise over 15 minutes with sodium cyanoborohydride (0.25 g, 4 mmole). After 2 hours the solution was diluted with water (50 ml), basified by addition of Na2CO3 and then extracted with ethyl acetate (2×50 ml). The combined extract was dried (Na2SO4), and concentrated in vacuo to leave the title compound as a brown oil (0.37 g, 73%).

Workup

  1. extractionextracted with ethyl acetate (2×50 ml)
  2. extractionThe combined extract
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d63bde5f192042b6a4da13635eb7910f
Source dataset
uspto-grants-1999_03
Patent number
US05889022

Reaction notes

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