Sodium Bicarbonate → HCID 67300937, compound

HRID 1015429Notes

Reaction equation

HRID 1015429 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH:15]=[CH:16][NH:17]3)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][NH:17]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 67301289HCID 67301289, compound

Product 1

HCID 67300937HCID 67300937, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-[5-(4-chloro-phenoxy)-pentyloxy]-1H-indole (1.72 g, 5.2 mmol) in 20 mL acetic acid was added sodium cyanoborohydride (2.61 g, 41.6 mmol). After stirred overnight at room temperature, the reaction mixture was treated with saturated aqueous sodium bicarbonate solution (50 mL). The solution was then extracted with ethyl acetate (3×50 mL), and the combined organic phases were washed with brine, dried over MgSO4, and concentrated to give a crude product as a white solid. The crude product was purified by silica gel column chromatography to give 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-1H-indole (600 mg, 1.80 mmol, 35%) as a white solid.

Workup

  1. extractionThe solution was then extracted with ethyl acetate (3×50 mL)
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a crude product as a white solid
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b52fadc780824546a40ffb3f93a7040a
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

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