Sodium hydride → Methyl 4-(2-Pyrrolidinylethyloxy)benzoate

HRID 265900Notes

Reaction equation

HRID 265900 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:4][CH3:5])[CH3:2].Cl[CH2:19]CN1CCCC1.Cl.[H-].[Na+]>CN(C=O)C>[N:3]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:19])=[O:14])=[CH:16][CH:17]=2)[CH2:4][CH2:5][CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 134390874-[2-(Diethylamino)ethoxy]benzoic acid

Product 1

HCID 18617411Methyl 4-(2-Pyrrolidinylethyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 23-2 (2 g, 11.8 mmol) and chloroethylpyrrolidine·HCl (Aldrich) (1.8 g, 11.8 mmol) were treated with NaH (0.94 g, 23.6 mmol) in DMF (30 mL) as described for 27-1 to give 27-6 as a clear oil. Rf (10% MeOH/CHCl3 saturated with NH3) 0.4

Sources & evidence

ORD record
ord-ee375870410c44d6a74c6035867c4f20
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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