4-Fluorobenzoyl chloride → 8-Methoxy-2-(2-(4-fluorobenzamido)ethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

HRID 5349

Reaction equation

[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][CH2:16][NH2:17])[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:25])=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl.C(N(CC)CC)C>[ClH:25].[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][CH2:16][NH:17][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=3)[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

Participants

Conditions

Temperature: -20 °C

Procedure

The product from Example 17 (0.95 g) was dissolved in 50 ml methylene chloride and 1.5 ml triethyl amine. The solution was cooled to -20° C. and 0.59 ml p-fluorobenzoyl chloride was added. After 30 min, the reaction was quenched in 5% NaHCO3 and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), evaporated, and the product was dissolved in ether and treated with ethereal HCl and then evaporated to dryness. The resulting product was recrystallized from ethyl acetate and ether to yield 0.772 g of the desired product as a white solid, mp: 197°-8° C. NMR (d6DMSO) δ2.60-3.10 (m, 3H), 3.00-3.50 (m, 4H), 3.59 (m, 2H), 3.78 (s, 3H), 3.82-4.22 (m, 3H), 6.83 (d, 1H), 6.87 (d, 1H), 7.23 (t, 1H), 7.34 (m, 2 H), 8.00 (m, 2H).

Workup

customthe reaction was quenched in 5% NaHCO3
extractionextracted with ethyl acetate
dry with materialThe organic extracts were dried (Na2SO4)
customevaporated
dissolutionthe product was dissolved in ether
additiontreated with ethereal HCl
customevaporated to dryness
customThe resulting product was recrystallized from ethyl acetate and ether

Sources & evidence

ORD record: ord-f54e63fe817945f5aca1b6509ef67a57
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244888

Linked notes

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