3,3-Dimethylbutylamine → HCID 12094487, compound

HRID 1168627Notes

Reaction equation

HRID 1168627 reaction equation
[CH2:1]([O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10]C=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:17][C:18]([CH3:23])([CH3:22])[CH2:19][CH2:20][NH2:21].O.OC1C2N=N[NH:31]C=2C=CC=1>CN(C)C=O.C(OCC)(=O)C>[CH3:17][C:18]([CH3:23])([CH3:22])[CH2:19][CH2:20][NH:21][C:12]([C:11]1[CH:10]=[N:31][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:16][CH:15]=1)=[O:13]

Participants

6

Reactant 3

HCID 197093,3-DimethylbutylamineHCID 170235Benzoyl chloride, 4-(hexyloxy)-HCID 178526939HCID 178526939, compound

Product 1

HCID 12094487HCID 12094487, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 4 (223 mg, 1.0 mmol) in dimethylformamide (2.5 mL) under argon at room temperature was treated with 3,3-dimethylbutyl amine (111 mg, 1.1 mmol), ethyl-3-(3-dimethylamino)-propylcarbodiimide hydrochloride (327 mg, 1.1 mmol) and hydroxybenzotriazole monohydrate (148 mg, 1.1 mmol) and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with 10% citric acid, water, dilute sodium bicarbonate, water and brine, dried (anhydrous mnagnesium sulfate) and concentrated to give an oil. Flash chromatography on silica gel and elution with ethyl acetate/hexanes (1:4) gave an oil (274 mg) that slowly solidified, mp 75-76.5° C. Analysis calculated for C18H30N2O2: C, 70.55; N, 9.87; N, 9.14. Found: C, 70.46; H, 10.06; N, 9.02.

Workup

  1. washwashed with 10% citric acid, water, dilute sodium bicarbonate, water and brine
  2. dry with materialdried (anhydrous mnagnesium sulfate)
  3. concentrationconcentrated
  4. customto give an oil
  5. washFlash chromatography on silica gel and elution with ethyl acetate/hexanes (1:4)

Sources & evidence

ORD record
ord-e285bca55c5a42119fc467a7bef7fa73
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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