Sodium Hydroxide → 5-Chloro-2,3-dihydro-6-(2-dimethylaminoethoxy)-1H-indole

HRID 399266Notes

Reaction equation

HRID 399266 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[NH:7][CH:6]=[CH:5]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[NH:7][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 540864225-Chloro-6-(2-dimethylaminoethoxy)-1H-indole

Product 1

HCID 543796875-Chloro-2,3-dihydro-6-(2-dimethylaminoethoxy)-1H-indoleYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

5-Chloro-6-(2-dimethylaminoethoxy)-1H-indole (D8, 0.2 g, 0.008 mol) in glacial acetic acid (5 ml) was treated with sodium cyanoborohydride (0.25 g, 0.004 mol ) at room temperature with stirring for 1 h. The mixture was diluted with water and basified with 10% aq NaOH. The product was extracted into CH2Cl2, and the combined extracts dried (Na2SO4) and concentrated in vacuo to give the title compound as a brown oil (0.21 g, 100%)

Workup

  1. extractionThe product was extracted into CH2Cl2
  2. dry with materialthe combined extracts dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-475c7201ebb848a4bcf92bf62337a181
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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