Triethylamine → HCID 20231732, compound

HRID 2290171Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH2:7].C(N(CC)CC)C.[F:15][C:16]([F:37])([F:36])[C:17]1[CH:18]=[CH:19][C:20]([O:23][C:24]2[CH:35]=[CH:34][C:27]([O:28][CH:29]([CH3:33])[C:30](Cl)=[O:31])=[CH:26][CH:25]=2)=[N:21][CH:22]=1>ClCCl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:30](=[O:31])[CH:29]([O:28][C:27]1[CH:26]=[CH:25][C:24]([O:23][C:20]2[CH:19]=[CH:18][C:17]([C:16]([F:36])([F:37])[F:15])=[CH:22][N:21]=2)=[CH:35][CH:34]=1)[CH3:33]

Participants

Conditions

Temperature: 5 °C

Procedure

1,3-Dioxolan-2 ylmethylamine (4 grams; 0.04 mol), triethylamine (5 ml) and dichloromethane (150 ml) were placed in a 3-necked glass reaction flask equipped with stirrer, thermometer and reflux condenser and cooled to 5° C. 2[4-(5-Trifluoromethyl-2-pyridinyloxy)-phenoxy]propanoic acid chloride (9 grams; 0.027 mol) in dichloromethane (30 ml) was added in a five minute time period. The reaction mixture was stirred for 1 hour at 5° C.-20° C., washed with water, passed through phase separating paper and concentrated to a dark gum (10.5 grams). The product was chromatographed through Florisil clay (100 ml), using hexane-ethyl acetate solvent mixtures. The desired product was isolated as a yellow gum (3.0 grams) and had the following elemental analysis:

Workup

customequipped with stirrer
temperaturethermometer and reflux condenser
washwashed with water
customseparating paper
concentrationconcentrated to a dark gum (10.5 grams)
customThe product was chromatographed through Florisil clay (100 ml)

Sources & evidence

ORD record: ord-7177c1241edf4e85884978b131cd710c
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04615728

Reaction notes

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