Triethylamine → Bicyclo [2.2.2]octane-1-carboxylic acid (4-{isopropyl-[2-(2-methoxyphenyl)ethyl]amino}butyl)amide

HRID 1938150Notes

Reaction equation

[C:1]12([C:9]([OH:11])=O)[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.S(Cl)(Cl)=O.[CH:16]([N:19]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])([CH3:18])[CH3:17].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl.CCCCCC.C(OCC)(=O)C.C(N(CC)CC)C>[CH:16]([N:19]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:9]([C:1]12[CH2:2][CH2:3][CH:4]([CH2:5][CH2:6]1)[CH2:7][CH2:8]2)=[O:11])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

Bicyclo[2.2.2]octane-1-carboxylic acid (0.53 g, 3.4 mmol), and thionyl chloride (1 ml, 13 mmol) dissolved in 10 ml toluene, were heated at 80° C. for 3 h. The solvent was partly removed and the residue added dropwise to a solution of 4-{isopropyl-[2-(2-methoxyphenyl)-ethyl]-aminobutylamine (1.2 g, 4.5 mmol) and triethylamine (3 ml, 20 mmol) in 10 ml methylene chloride at 0° C. and stirred for 1 h at room temperature. The mixture was charged on a silica gel column and eluated with hexane/ethyl acetate/triethylamine (16:4:1) to yield 1.1 g (86%) of an oil.

Workup

customThe solvent was partly removed
additionThe mixture was charged on a silica gel column

Sources & evidence

ORD record: ord-8513eec8851041ae8f28b5e3565e9da6
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693630

Reaction notes

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