Potassium Iodide → HCID 69529877, compound

HRID 1814429Notes

Reaction equation

HRID 1814429 reaction equation
[CH:1]1([NH:11][CH2:12][CH2:13][CH2:14][N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:35][CH2:36][CH2:37][C:38]#[N:39]>CC#N>[C:19]1(=[O:20])[N:15]([CH2:14][CH2:13][CH2:12][N:11]([CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[CH2:35][CH2:36][CH2:37][C:38]#[N:39])[C:16](=[O:25])[C:17]2=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]12

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 22506225HCID 22506225, compound

Product 1

HCID 69529877HCID 69529877, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-[3-(1,2,3,4-tetrahydro-1-naphthylamino)propyl]phthalimide (569 mg, 1.7 mmol), potassium carbonate (709 mg, 5.1 mmol) and potassium iodide (280 mg, 1.7 mmol) in CH3CN (20 ml) was added 4-bromobutyronitrile (754 mg, 5.1 mmol). The mixture was refluxed under stirring for 18 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue was chromatographed on silica gel (eluting with 20% ethyl acetate/chloroform) to afford 4-[[(3-phthalimido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butyronitrile (336 mg, 50%): MS(ES+) m/e 402 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.82 (dd, J=5.4, 2.9 Hz, 2H), 7.70 (m, 2H), 7.60 (d, J=7.6 Hz, 1H), 7.11 (m, 1H), 7.02 (m, 2H), 3.95 (m, 1H), 3.78 (m, 1H), 3.59 (m, 1H), 2.73 (m, 2H), 2.64 (m, 1H), 2.51 (m, 4H), 2.35 (m, 1H), 1.98 (m, 2H), 1.83 (m, 4H), 1.63 (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 20% ethyl acetate/chloroform)

Sources & evidence

ORD record
ord-834675c9ef814923889244303d69d3f2
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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