Sodium Hydroxide → HCID 5138807, compound

HRID 1278081Notes

Reaction equation

HRID 1278081 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[NH:11][C:10](=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21577756HCID 21577756, compound

Product 1

HCID 5138807HCID 5138807, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Heat 1.05 g of 5-(4-chlorobenzyl)pyrrolidin-2-one and 0.2 g of lithium aluminum hydride under reflux for 20 hours in 20 ml of tetrahydrofuran. Effect decomposition of the reaction product by admixing it with ice water. Then add 5 ml of 6 N sodium hydroxide solution to the resulting admixture and extract the thus-prepared base with diethyl ether. After drying the ether extract over sodium sulfate, concentrate it to obtain 0.7 g of the title compound as an oil. Convert the oil into the corresponding hydrochloride with methanol/ethereal hydrochloric acid; yield: 580 mg; m.p. of the hydrochloride 189° to 192°.

Workup

  1. extractionextract the thus-prepared base with diethyl ether
  2. dry with materialAfter drying the ether
  3. extractionextract over sodium sulfate
  4. concentrationconcentrate it

Sources & evidence

ORD record
ord-6e9922e0f0324b97b1e811107029e2b6
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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