Chloroform → HCID 57888632, compound

HRID 1820309Notes

Reaction equation

[C:1]1([CH3:16])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Br[CH2:18][CH2:19][C:20]1([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>CN(C)C=O>[C:3]1([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:16])[C:2]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:18][CH2:19][C:20]2([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 4-(mesitylamino)piperidine (250 mg, 1.15 mmol), methyl [1-(2-bromoethyl)cyclohexyl]acetate (371 mg, 1.38 mmol) and potassium carbonate (318 mg, 2.3 mmol) in N,N-dimethylformamide (3 mL) was stirred at 80° C. for 10 hours. Chloroform (10 mL) was added to the reaction mixture, the insoluble portion was filtered out, and the filtrate was concentrated under reduced pressure. The residue was dissolved in xylene (10 mL) and concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (10 g Merck Art 9385, hexane:ethyl acetate=7:3-chloroform:methanol=10:1) to obtain the title compound as a brown oil (243 mg) (53% yield).

Workup

filtrationthe insoluble portion was filtered out
concentrationthe filtrate was concentrated under reduced pressure
dissolutionThe residue was dissolved in xylene (10 mL)
concentrationconcentrated under reduced pressure
customThe residue was then purified by silica gel column chromatography (10 g Merck Art 9385, hexane:ethyl acetate=7:3-chloroform:methanol=10:1)

Sources & evidence

ORD record: ord-15ffe54b10c74b2db3845af7a037251c
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601843B2

Reaction notes

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