Phenethyl bromide → (S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992277Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)=[O:8])[CH2:2]1.Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:22]1([CH2:21][CH2:20][N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]34[CH2:18][CH:13]5[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]5)[CH2:10]3)[CH2:16]4)=[O:8])[CH2:2]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 70 °C

Procedure

(S)-N-(Pyrrolidin-3-yl)-1-adamantanecarboxamide (3.9 g) and 2-bromoethylbenzene (2.9 g) were dissolved in DMF, and potassium carbonate was added. The mixture was stirred under heating at 70° C. for 5 hours, and after the completion of the reaction, the solvent was evaporated under reduced pressure. Ethyl acetate was added to the obtained residue and the mixture was washed with saturated brine. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (chloroform:methanol=30:1). The obtained eluate was concentrated and IPE was added. The precipitated crystals were collected by filtration to give (S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide (4.3 g), melting point 119-121° C.

Workup

customafter the completion of the reaction
customthe solvent was evaporated under reduced pressure
additionEthyl acetate was added to the obtained residue
washthe mixture was washed with saturated brine
customThe solvent was evaporated under reduced pressure
concentrationThe obtained eluate was concentrated
additionIPE was added
filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-b412e57ab30f49e2bcc55d8f0244a90a
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468998B1

Reaction notes

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