N-Methylpropylamine → 5-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 1436626Notes

Reaction equation

HRID 1436626 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:7]([C:8]([OH:10])=O)[CH:6]=1)[CH3:2].[CH3:17][NH:18][CH2:19][CH2:20][CH3:21].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:7]([C:8]([N:18]([CH3:17])[CH2:19][CH2:20][CH3:21])=[O:10])[CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 12315N-MethylpropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 210858293-(Ethoxycarbonyl)-5-(hydroxymethyl)benzoic acid

Product 1

HCID 688164795-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl esterYield 40.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Stir a solution of 5-hydroxymethyl-isophthalic acid monoethyl ester (1.9 g, 8.4 mmol), N-methylpropylamine (947 μl, 9.2 mmol), 1-hydroxybenzotriazole (1.24 g, 9.2 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.77 g, 9.2 mmol) in a mixture of dichloromethane (12 mL) and DMF (12 mL) at room temperature for 1.5 h. Concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound (950 mg, 40% yield).

Workup

  1. concentrationConcentrate
  2. custompurify
  3. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-2d8590c385a14971b1e2d2a829db6cb1
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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