تفاعل #1741869

معادلة التفاعل

sodium hydroxide

lithium aluminum hydride

aluminum chloride

Dicyclohexylcarbodiimide

(R)-3-phenyl-3-cyclohexenecarboxylic acid

2-pyridylpiperazine

hydroxybenzotriazole hydrate

→

(R)-1-[(3-Phenyl-3-cyclohexen-1-yl)methyl]-4-(2-pyridinyl)piperazine

المردود 32.2%

المذيبات

Water

tetrahydrofuran

ether

tetrahydrofuran

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture is filtered
2. 2
   أخرىevaporated
3. 3
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
4. 4
   ترشيحfiltered
5. 5
   غسيلwashed with saturated sodium bicarbonate, 5% citric acid, 2N sodium carbonate, brine
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated
9. 9
   أخرىto leave a yellow solid
10. 10
    workup.STIRRINGstirred for 2 hours
11. 11
    ترشيحthe mixture filtered
12. 12
    غسيلwashed with brine
13. 13
    تجفيفdried over magnesium sulfate
14. 14
    ترشيحfiltered
15. 15
    أخرىevaporated to a yellow oil
16. 16
    أخرىThis oil is purified by medium pressure liquid chromatography on silica gel eluting with 50% ethyl acetate in hexane

الإجراء التجريبي

Dicyclohexylcarbodiimide (0.506 g) in dichloromethane (10 mL) is added to (R)-3-phenyl-3-cyclohexenecarboxylic acid (0.414 g, Example D), 2-pyridylpiperazine (0.410 g) and hydroxybenzotriazole hydrate (0.332 g) in dichloromethane (40 mL) and stirred overnight. The mixture is filtered and evaporated. The residue is dissolved in ethyl acetate, filtered, washed with saturated sodium bicarbonate, 5% citric acid, 2N sodium carbonate, brine, dried over magnesium sulfate, filtered, and evaporated to leave a yellow solid. This solid is dissolved in tetrahydrofuran (5 mL) and added to lithium aluminum hydride (78 mg) in tetrahydrofuran (5 mL) pretreated with aluminum chloride (90 mg) in ether (5 mL) at 0° C. and stirred for 2 hours. Water (0.1 mL) and 25% sodium hydroxide (0.4 mL) are added and the mixture filtered, washed with brine, dried over magnesium sulfate, filtered, and evaporated to a yellow oil. This oil is purified by medium pressure liquid chromatography on silica gel eluting with 50% ethyl acetate in hexane to give 0.22 g of (R)-1-[(3-Phenyl-3-cyclohexen-1-yl)methyl]-4-(2-pyridinyl)piperazine as an off-white solid; mp 106°-108° C.

المصدر