Sodium Hydroxide → 4-[(1-Methylpyrrolidin-2-yl)methyl]aniline

HRID 1278083Notes

Reaction equation

HRID 1278083 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[N:11]([CH3:12])[C:10](=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][N:11]2[CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 234525985-(4-Aminobenzyl)-1-methylpyrrolidin-2-one

Product 1

HCID 131869044-[(1-Methylpyrrolidin-2-yl)methyl]aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boil 2.04 g of 5-(4-aminobenzyl)-1-methylpyrrolidin-2-one and 0.7 g of lithium aluminum hydride under reflux for 20 hours in 20 ml of tetrahydrofuran. Decompose the resulting reaction product by admixing it with ice water. After adding 10 ml of 6 N sodium hydroxide solution to the decomposed product, extract it with diethyl ether. Dry the ether extract over sodium sulfate and concentrate it to obtain the title compound in free-base form. Convert the thus-obtained base into the dihydrochloride [m.p. (from methanol/ether)>242° (decomp.)] with methanol/ethereal hydrochloric acid.

Workup

  1. customthe resulting reaction product
  2. extractionextract it with diethyl ether
  3. dry with materialDry the ether
  4. extractionextract over sodium sulfate
  5. concentrationconcentrate it

Sources & evidence

ORD record
ord-9ce85bc1244541b58f3a82f1a9a0411a
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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