Acetic Acid → HCID 178489625, compound

HRID 1872852Notes

Reaction equation

HRID 1872852 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[CH3:18][O:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[O:22][CH2:23][CH2:24][NH2:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C@@H:11]1[CH2:16][CH2:15][C@H:14]([NH:25][CH2:24][CH2:23][O:22][C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[O:19][CH3:18])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 5049666Sodium triacetoxyborohydrideHCID 107046834-(5-Fluoro-1H-indol-3-YL)cyclohexanone

Product 1

HCID 178489625HCID 178489625, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-(5-fluoro-1H-indol-3-yl)-cyclohexanone (0.38 g, 1.6 mmol), [2-(2-methoxy-phenoxy)-ethyl]-amine (0.27 g, 1.6 mmol), sodium triacetoxyborohydride (0.5 g, 2.2 mmol) and acetic acid (0.06 ml, 1.8 mmol) in 1,2-dichloroethane (8 ml) was allowed to stir at room temperature for 4 hours. The reaction was quenched with 1N sodium hydroxide (10 ml), extracted with methylene chloride (3×60 ml) and washed with brine (3×60 ml). The organic layer was dried over anhydrous sodium sulfate and filtered. Chromatography (10% methanol-ethyl acetate) afforded 0.43 g (71%) of product as a white solid.

Workup

  1. customThe reaction was quenched with 1N sodium hydroxide (10 ml)
  2. extractionextracted with methylene chloride (3×60 ml)
  3. washwashed with brine (3×60 ml)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-3935624c78a64805903819c7b76ea367
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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