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

HRID 992277
Notes
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Reaction equation

HRID 992277 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 49760538(S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide

Product 1

HCID 9841449(S)-N-(1-(2-phenylethyl)pyrrolidin-3-yl)-1-adamantanecarboxamideYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customafter the completion of the reaction
  2. customthe solvent was evaporated under reduced pressure
  3. additionEthyl acetate was added to the obtained residue
  4. washthe mixture was washed with saturated brine
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe obtained eluate was concentrated
  7. additionIPE was added
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes