Triethylamine → HCID 14535909, compound

HRID 1904923Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[F-:11].[K+].[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]([CH3:25])[CH2:17][C:18]2([CH3:24])[CH3:23].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:11][C:2]1[C:3]([C:4]([NH:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]([CH3:25])[CH2:17][C:18]3([CH3:24])[CH3:23])=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

Conditions

Temperature: 155 °C

Procedure

To a solution of 2.6 g (14.8 mmol) of 2-chloronicotinic acid chloride in 15 ml of sulforan was added 2.6 g (46.4 mmol) of potassium fluoride, and the mixture was stirred under heating at 155° C. for 6 hours. After cooling, precipitated crystals were filtered out. The filtrate was added dropwise to a solution of 2 g (11.4 mmol) of 4-amino-1,1,3-trimethylindane and 1.6 g (15.8 mmol) of triethylamine in 10 ml of toluene under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was then added with 30 ml of toluene, washed with water, dried over Glauber's salt and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=4/1) to obtain 1.6 g of oil (Compound No. 9 shown in Table 2) in a yield of 47%.

Workup

temperatureAfter cooling
customprecipitated crystals
filtrationwere filtered out
stirringthe mixture was stirred at room temperature for 2 hours
washwashed with water
dry with materialdried over Glauber's salt
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (eluent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-94c310c205e049c09c831574fe58c834
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04840959

Reaction notes

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