3,3-Dimethylbutylamine → HCID 22992905, compound

HRID 1168624Notes

Reaction equation

HRID 1168624 reaction equation
CO[C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-])=O)=[CH:6][CH:5]=1.[CH3:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][NH2:18].O.OC1C2N=N[NH:28]C=2C=CC=1>CN(C=O)C.C(OCC)(=O)C>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([NH:18][CH2:17][CH2:16][C:15]([CH3:20])([CH3:19])[CH3:14])=[O:13])=[CH:12][CH:11]=1)#[N:28]

Participants

6

Reactant 3

HCID 197093,3-DimethylbutylamineHCID 36144541,4-Benzenedicarboxylic acid, methyl esterHCID 178526939HCID 178526939, compound

Product 1

HCID 22992905HCID 22992905, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-cyanobenzoic acid (1, 735 mg, 5.0 mmol) in 12 mL of DMF under argon at room temperature was treated 3,3-dimethylbutylamine (2, 505 mg, 5.0 mmol), ethyl-3-(3-dimethylamino)-propyl carbodiimide hydrochloride (1.5 g, 5.0 mmol) and hydroxybenzotriazole monohydrate (685 mg, 5.0 mmol) and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with 10 percent citric acid, water, dilute sodium bicarbonate, water and brine. The dried (anhydrous magnesium sulfate) organic fraction was concentrated to give 1.5 g. Flash chromatography on 150 mL of EM-60 silica gel, eluting with ethyl acetate/hexanes (1:4) gave the title compound (1.06 g, 92%), mp 154-157° C. Analysis calculated for C14H18N2O: C, 73.01; H, 7.88; N, 12.16. Found: C, 73.00; H, 7.92; N, 12.17.

Workup

  1. washwashed with 10 percent citric acid, water, dilute sodium bicarbonate, water and brine
  2. dry with materialThe dried (anhydrous magnesium sulfate) organic fraction
  3. concentrationwas concentrated
  4. customto give 1.5 g
  5. washFlash chromatography on 150 mL of EM-60 silica gel, eluting with ethyl acetate/hexanes (1:4)

Sources & evidence

ORD record
ord-19d63a9d65904d528a5236c78d52f9e3
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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