4-Aminobenzoic Acid → 1-(4-Aminobenzoyl)-3-dimethylamino-pyrrolidine

HRID 1176056Notes

Reaction equation

HRID 1176056 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:18])[CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1.CN(C)CCCN=C=NCC>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:15]2[CH2:16][CH2:17][CH:13]([N:12]([CH3:18])[CH3:11])[CH2:14]2)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 225674711-(4-Aminobenzoyl)-3-dimethylamino-pyrrolidineYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-aminobenzoic acid (1.4 g, 10 mmol), 3-(dimethylamino)-pyrrolidine (1.5 g, 13 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (2.5 g, 13 mmol) in CH2Cl2 is stirred at room temperature for 16 h, diluted with CH2Cl2, washed with water, dried over MgSO4 and concentrated in vacuo to give the title compound (1.1 g), identified by NMR analysis.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2718d3fc111643df804e2b37dedaa82f
Source dataset
uspto-grants-2010_11
Patent number
US07842715B2

Reaction notes

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