Acetic Acid → HCID 178488082, compound

HRID 992078Notes

Reaction equation

HRID 992078 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[NH:19]1[C:27]2[C:22](=[C:23]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C@H:12]1[CH2:17][CH2:16][C@@H:15]([N:31]2[CH2:32][CH2:33][N:28]([C:23]3[CH:24]=[CH:25][CH:26]=[C:27]4[C:22]=3[CH:21]=[CH:20][NH:19]4)[CH2:29][CH2:30]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 105382004-(5-Methoxy-1H-indol-3-YL)cyclohexanone

Product 1

HCID 178488082HCID 178488082, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-(5-methoxy-1H-indol-3-yl)-cyclohexanone (1.2 g, 5 mmol), 1-(indol-4-yl)piperazine (1 g, 5 mmol), sodium triacetoxyborohydride (1.47 g, 6.2 mmol) and acetic acid (0.28 ml, 4 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 (2.5% methanol-ethyl acetate) afforded 1.18 g (55%) of product as a white solid: mp 105-108° C.

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-9add60c38189458ea80020ddfa39ba97
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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