Acetic Acid → 2-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol

HRID 388354Notes

Reaction equation

HRID 388354 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)=O.[NH2:12]C(O)C.[C:16]([OH:19])(=O)[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[NH:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:1][NH:12][CH2:17][CH2:16][OH:19])[CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 522583Acetaldehyde ammoniaHCID 2734629Indole-7-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 219500502-[(1H-Indol-7-ylmethyl)amino]-ethan-1-ol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 7-formyl indole (2.4 g, 16.6 mmol) in 1,2-dichloroethane (60 mL) was added aminoethanol (1.2 mL, 19.8 mmol) followed by glacial acetic acid (2.0 mL) and sodium triacetoxyborohydride (3.5 g, 16.6 mmol). The reaction mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was quenched by addition of water (10 mL) and 1.0 M sodium hydroxide (10 mL). The organic layer was then separated and the aqueous layer extracted with 1,2-dichloroethane (40 mL). The combined organic extracts were washed with saturated sodium bicarbonate (2×30 mL), water (2×50 mL), dried over anhydrous sodium sulfate and evaporated to dryness. 2-[(1H-indol-7-ylmethyl)-amino]-ethanol (4.4 g) was obtained as an oil LCMS (M+H)=189.

Workup

  1. customThe reaction mixture was quenched by addition of water (10 mL) and 1.0 M sodium hydroxide (10 mL)
  2. customThe organic layer was then separated
  3. extractionthe aqueous layer extracted with 1,2-dichloroethane (40 mL)
  4. washThe combined organic extracts were washed with saturated sodium bicarbonate (2×30 mL), water (2×50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c47f1283ed6e4ac3b05e3e9b4ad32df3
Source dataset
uspto-grants-2013_02
Patent number
US08377927B2

Reaction notes

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