Water → HCID 22141327, compound

HRID 1826430Notes

Reaction equation

Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)[CH3:11].C(=O)([O-])O.[Na+].[C:25]1([CH2:31][CH2:32][CH2:33][NH2:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O>[CH3:11][C:4]1([C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[C:18]#[N:19])[CH:5]2[CH:3]1[CH2:2][N:34]([CH2:33][CH2:32][CH2:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:6]2=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 3-(chloromethyl)-2-(3-cyanophenyl)-2-methylcyclopropanecarboxylate (Preparation 35, 170 mg, 0.62 mmol) in N,N-dimethylformamide (6.0 ml) at room temperature was added sodium hydrogen carbonate (52 mg, 0.62 mmol) followed by 3-phenylpropylamine (0.35 ml, 2.47 mmol). The mixture was heated at 100° C. for 6 h and under reflux for 5 h. After the mixture had cooled to room temperature, water (4 ml) was added and the aqueous layer was extracted with diethyl ether (3×4 ml). The combined ethereal extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude oil was purified by silica column chromatography eluting with a gradient of hexane:ethyl acetate (50:50 to 0:100) to afford the title compound (80 mg, 40%) as a colourless oil.

Workup

temperatureunder reflux for 5 h
temperatureAfter the mixture had cooled to room temperature
extractionthe aqueous layer was extracted with diethyl ether (3×4 ml)
dry with materialThe combined ethereal extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude oil was purified by silica column chromatography
washeluting with a gradient of hexane:ethyl acetate (50:50 to 0:100)

Sources & evidence

ORD record: ord-38540e0a3d3d4de7be92cc5f2ee54769
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049444B2

Reaction notes

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