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

HRID 2416568Notes

Reaction equation

HRID 2416568 reaction equation
[Cl-].[C:2]([O:13][CH3:14])(=[O:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=O)=[CH:5][CH:4]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>ClCCl>[N:15]1([C:7]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([O:13][CH3:14])=[O:12])=[CH:11][CH:10]=2)=[O:9])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 22493623Monomethyl terephthalate chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

29.0 g (0.146 mol) of monomethyl terephthalate chloride was reacted with 14.2 g (200 mmol) of pyrrolidine and 21.0 g (208 mmol) of triethylamine in 350 ml of dichloromethane. After the treatment in an ordinary manner, methyl 4-(1-pyrrolidylcarbonyl)benzoate was obtained. 29.0 g of the ester 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 evaporated. 1 N hydrochloric acid was added to the residue and the obtained mixture was treated with dichloromethane as the extraction solvent in an ordinary manner to obtain the title compound.

Sources & evidence

ORD record
ord-435f7a786c794948a4aaf27245e89b2b
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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