Acetic Acid → HCID 62997896, compound

HRID 751528Notes

Reaction equation

HRID 751528 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][C:34]=2[CH:36]=O)[CH:29]=[CH:28]1>ClCCCl.ClCCl>[CH2:1]([NH:8][CH2:36][C:34]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:35]=1[NH:27][CH:28]=[CH:29]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 2734629Indole-7-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 62997896HCID 62997896, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Add benzyl amine (7.5 g, 69.7 mmol), sodium triacetoxyborohydride (20.7 g, 97.5 mmol) and acetic acid (6.0 mL, 104.6 mmol) to a solution of 1H-indole-7-carboxaldehyde (10.1 g, 69.7 mmol) in 1,2-dichloroethane (100 mL). Stir at ambient temperature for 24 hours. Dilute with dichloromethane and wash the organic layer with water. Dry with magnesium sulfate and concentrate. Purify by chromatography (silica gel; ethyl acetate/methanol; 10:0.3 to 10:1) to yield a light yellow solid (13.5 g, 82%). MS (ESI) m/z 237 (M+H)+.

Workup

  1. washwash the organic layer with water
  2. dry with materialDry with magnesium sulfate
  3. concentrationconcentrate
  4. customPurify by chromatography (silica gel; ethyl acetate/methanol; 10:0.3 to 10:1)

Sources & evidence

ORD record
ord-bc3d2dda01a14404a156fc5d3ca9bdb4
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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