HCID 15029754, compound → HCID 14231162, compound

HRID 1707372Notes

Reaction equation

HRID 1707372 reaction equation
CC(C)([O-])C.[K+].[N:7]1([CH:12]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH2:15][CH2:16]Cl)[CH:11]=[CH:10][N:9]=[CH:8]1>O1CCCC1>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([C:12]2([N:7]3[CH:11]=[CH:10][N:9]=[CH:8]3)[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:19][CH:20]=1)#[N:23]

Participants

4

Reactant 2

HCID 15029754HCID 15029754, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14231162HCID 14231162, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of potassium tert-butoxide (1.10 g) in tetrahydrofuran (50 mL) is added dropwise to a solution of 4-[1-(1-imidazolyl)-5-chloropentyl]benzonitrile (2.50 g) in tetrahydrofuran at 0° (ice-bath). The reaction is allowed to proceed at 0° for 30 minutes and is then allowed to warm to room temperature during 3 hours. The reaction is then quenched with water (100 mL) and the mixture is subsequently extracted with ethyl acetate (100 mL). The organic extract is extracted with 3 N hydrochloric acid (3×30 mL) and the combined acid extracts are made basic with 6 N sodium hydroxide. The crude product is extracted into ethyl acetate (3×30 mL) and the combined extracts are dried (MgSO4) and evaporated to afford 1-(4-cyanophenyl) -1-(1-imidazolyl)cyclopentane as an oil. The compound is dissolved in acetone and treated with ethereal HCl to afford the hydrochloride salt, m.p. 217°-219°.

Workup

  1. customThe reaction is then quenched with water (100 mL)
  2. extractionthe mixture is subsequently extracted with ethyl acetate (100 mL)
  3. extractionThe organic extract
  4. extractionis extracted with 3 N hydrochloric acid (3×30 mL)
  5. extractionThe crude product is extracted into ethyl acetate (3×30 mL)
  6. dry with materialthe combined extracts are dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-f2ba440c7da4480bb99c1d279053c251
Source dataset
uspto-grants-1994_10
Patent number
US05352795

Reaction notes

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