Potassium Carbonate → HCID 22506255, compound

HRID 1814413Notes

Reaction equation

HRID 1814413 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31]>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:18][CH2:19][CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 674302-(4-Chlorophenyl)ethylamine

Product 1

HCID 22506255HCID 22506255, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-(4-chlorophenyl)ethylamine (1.56 g, 10 mmol) and potassium carbonate (2.8 g, 20 mmol) in CH3CN (50 ml) was added N-(3-bromopropyl)phthalimide (3.0 g, 11 mmol). The mixture was refluxed under stirring for 16 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue was chromatographed on silica gel (eluting with 2.5% methanol/chloroform) to afford N-[3-[2-(4-chlorophenyl)ethylamino]propyl]phthalimide (2.28 g, 67%): MS(FD) m/e 343 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.84 (m, 2H), 7.71 (m, 2H), 7.24 (d, J=8.3 Hz, 2H), 7.11 (d, J=8.3 Hz, 2H), 3.74 (d, J=6.8 Hz, 2H), 2.82 (t, J=6.8 Hz, 2H), 2.73 (t, J=6.8 Hz, 2H), 2.66 (t, J=6.8 Hz, 2H), 1.84 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum to dryness
  4. customthe residue was chromatographed on silica gel (eluting with 2.5% methanol/chloroform)

Sources & evidence

ORD record
ord-024a722b57064da5879b457402cc19bc
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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