Triethylamine → Methyl 4-(pyrrolidine-1-carbonyl)benzoate

HRID 747782Notes

Reaction equation

HRID 747782 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10](Cl)=[O:11])=[CH:6][CH:5]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>ClCCl>[N:14]1([C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:13])=[CH:5][CH:6]=2)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 81850Methyl 4-(chlorocarbonyl)benzoate

Product 1

HCID 17178210Methyl 4-(pyrrolidine-1-carbonyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

29.0 g (0.146 mol) of 4-chlorocarbonyl benzoic acid monomethyl ester, 14.2 g (200 mmol) of pyrrolidine and 21.0 g (208 mmol) of triethylamine were reacted in 350 ml of dichloromethane. After the treatment in an ordinary manner, methyl 4-(1-pyrrolidylcarbonyl)benzoate was obtained. 29.0 g of this ester compound was hydrolyzed with 12.0 g of sodium hydroxide in a mixed solvent comprising 70 ml of water, 70 ml of methanol and 70 ml of tetrahydrofuran. After the completion of the reaction, the solvent was distilled off. After the addition of 1 N hydrochloric acid followed by the treatment with dichloromethane as the extractant in an ordinary manner, the title compound was obtained.

Sources & evidence

ORD record
ord-6ab4ef190f304f0c89a42b91205f1d6b
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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