HCID 20136522, compound → HCID 14231162, compound

HRID 579774Notes

Reaction equation

HRID 579774 reaction equation
[CH3:1]C(C)([O-])C.[K+].[N:7]1([CH:12]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:13][CH2:14][CH2:15]Cl)[CH:11]=[CH:10][N:9]=[CH:8]1>O1CCCC1>[C:21]([C:20]1[CH:23]=[CH:24][C:17]([C:12]2([N:7]3[CH:11]=[CH:10][N:9]=[CH:8]3)[CH2:1][CH2:15][CH2:14][CH2:13]2)=[CH:18][CH:19]=1)#[N:22]

Participants

4

Reactant 2

HCID 20136522HCID 20136522, 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)-4-chlorobutyl]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 3N hydrochloric acid (3×30 mL) and the combined acid extracts are made basic with 6N 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 3N 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-dec5a60b48db42918dd98393026fa697
Source dataset
uspto-grants-1988_06
Patent number
US04749713

Reaction notes

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