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

HRID 428561Notes

Reaction equation

HRID 428561 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13]C)[CH:7]=[C:6]2[CH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)#[N:2].[NH:22]1[C:30]2[C:25](=[C:26]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH3:13][CH: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:15]2[CH2:20][CH2:19][CH:18]([N:34]3[CH2:35][CH2:36][N:31]([C:26]4[C:25]5[CH:24]=[CH:23][NH:22][C:30]=5[CH:29]=[CH:28][CH:27]=4)[CH2:32][CH2:33]3)[CH2:17][CH2:16]2)=[CH:7]1)[CH3:37]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 5049666Sodium triacetoxyborohydrideHCID 184141234-(5-Cyano-1-n-propyl-3-indolyl)-cyclohexanone

Product 1

HCID 102268223-{(1,4-cis)-4-[4-(1H-Indol-4-yl)-piperazin-1-yl]-cyclohexyl}-1-isopropyl-1H-indole-5-carbonitrileYield 18%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 4-(5-cyano-1-n-propyl-indol-3-yl)-cyclohexanone (1.68 g, 6 mmol), 1-(indol-4-yl)piperazine (1.27 g, 6.3 mmol), sodium triacetoxyborohydride (1.84 g, 8.9 mmol) and acetic acid (0.94 ml, 16 mmol) in 1,2-dichloroethane (80 ml) was allowed to stir at room temperature overnight. The reaction was quenched with 1N sodium hydroxide (20 ml), extracted with methylene chloride (3×100 ml), and washed with brine (3×100 ml). The organic layer was dried over anhydrous sodium sulfate, and filtered. Chromatography (10% methanol-ethyl acetate) afforded 0.49 g (18%) of product as a white powder.

Workup

  1. customThe reaction was quenched with 1N sodium hydroxide (20 ml)
  2. extractionextracted with methylene chloride (3×100 ml)
  3. washwashed with brine (3×100 ml)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c70f393dec32439b80fd5c29f11e53e4
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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