Potassium Carbonate → 4-[4-(6-Fluoro-benzo[b]thiophen-3yl)-[1,4]diazapan-1-yl]butyronitrile

HRID 1986907Notes

Reaction equation

HRID 1986907 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([N:16]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:14][S:13][C:12]=2[CH:23]=1.Br[CH2:25][CH2:26][CH2:27][C:28]#[N:29]>C(#N)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([N:16]3[CH2:22][CH2:21][CH2:20][N:19]([CH2:25][CH2:26][CH2:27][C:28]#[N:29])[CH2:18][CH2:17]3)=[CH:14][S:13][C:12]=2[CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 231124871-(6-Fluoro-benzo[b]thiophen-3-yl)-[1,4]diazepane

Product 1

HCID 577225594-[4-(6-Fluoro-benzo[b]thiophen-3yl)-[1,4]diazapan-1-yl]butyronitrileYield 42.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add potassium carbonate (39.3 g, 284 mmol) to a solution of 1-(6-fluoro-benzo[b]thiophen-3-yl)-[1,4]diazepane (Example 4) (23.7 g, 95 mmol) and 4-bromobutyronitrile (21.0 g, 142 mmol) in acetonitrile (400 mL) and stir the mixture under reflux for 10 h. Filter the mixture, evaporate the solvent, and dissolve the residue in ethyl acetate (EtOAc). Wash with water and saturated sodium chloride solution, and dry the organic phase over MgSO4. Evaporate the solvent under vacuum, and purify the crude product by column chromatography (EtOAc/MeOH 9:1) to give 12.9 g of a yellow oil LC/MS, (LiChrospher 5μ, RP-18, 250 mm

Workup

  1. temperatureunder reflux for 10 h
  2. filtrationFilter the mixture
  3. customevaporate the solvent
  4. dissolutiondissolve the residue in ethyl acetate (EtOAc)
  5. washWash with water and saturated sodium chloride solution
  6. dry with materialdry the organic phase over MgSO4
  7. customEvaporate the solvent under vacuum
  8. custompurify the crude product by column chromatography (EtOAc/MeOH 9:1)

Sources & evidence

ORD record
ord-425816799d0c42dd937dc897a4c7406c
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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