Acetic Acid → HCID 178505571, compound

HRID 428556Notes

Reaction equation

HRID 428556 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)=[CH:5][NH:6]2.[NH:18]1[C:26]2[C:21](=[C:22]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:30]3[CH2:31][CH2:32][N:27]([C:22]4[CH:23]=[CH:24][CH:25]=[C:26]5[C:21]=4[CH:20]=[CH:19][NH:18]5)[CH2:28][CH2:29]3)[CH2:13][CH2:12]1)=[CH:5][NH:6]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 184141744-(4-Fluoro-1H-3-indolyl)-cyclohexanone

Product 1

HCID 178505571HCID 178505571, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-(4-fluoro-1H-indol-3-yl)-cyclohexanone (0.88 g, 3.8 mmol), 1-(indol-4-yl)piperazine (0.7 g, 3.5 mmol), sodium triacetoxyborohydride (1.1 g, 5.2 mmol) and acetic acid (0.4 ml, 7 mmol) in 1,2-dichloroethane (20 ml) was allowed to stir at room temperature overnight. 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 (5-7% methanol-ethyl acetate) afforded 1.14 g (79%) of product as a white foam.

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-2711d80e42524d4d88b90e239d8eb177
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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