Acetic Acid → 3-{(1,4-cis)-4-[4-(1H-Indol-4-yl)-piperazin-1-yl]-cyclohexyl}-1-methyl-1H-indole-5-carbonitrile

HRID 992080Notes

Reaction equation

HRID 992080 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[CH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)#[N:2].[NH:20]1[C:28]2[C:23](=[C:24]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH3:12][N:8]1[C:9]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[C:6]([CH:13]2[CH2:18][CH2:17][CH:16]([N:32]3[CH2:33][CH2:34][N:29]([C:24]4[C:23]5[CH:22]=[CH:21][NH:20][C:28]=5[CH:27]=[CH:26][CH:25]=4)[CH2:30][CH2:31]3)[CH2:15][CH2:14]2)=[CH:7]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 154812824-(5-Cyano-1-methyl-3-indolyl)cyclohexanone

Product 1

HCID 120195263-{(1,4-cis)-4-[4-(1H-Indol-4-yl)-piperazin-1-yl]-cyclohexyl}-1-methyl-1H-indole-5-carbonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-(5-cyano-1-methyl-3-indolyl)-cyclohexanone (0.75 g, 3 mmol), 1-(indol-4-yl)piperazine (0.6 g, 3 mmol), sodium triacetoxyborohydride (0.95 g, 4.5 mmol) and acetic acid (0.34 ml, 6 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 (10% methanol-ethyl acetate) afforded 0.73 g (56%) of product as a white solid: mp 274-275° 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-975001ebff884abdb44aaf2be294d127
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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