Acetonitrile → HCID 22506225, compound

HRID 1814419Notes

Reaction equation

HRID 1814419 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH:12]1([NH2:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1.[C:23](=O)([O-])[O-].[K+].[K+].[CH3:29][C:30]#N>>[CH:12]1([NH:22][CH2:23][CH2:30][CH2:29][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 180661,2,3,4-Tetrahydro-1-naphthylamine

Product 1

HCID 22506225HCID 22506225, compoundYield 74%

Procedure

N3-Bromopropyl)phthalimide (13.0 g, 48.5 mmol) was added to a mixture of 1,2,3,4-tetrahydro-1-naphthylamine (6.96 ml, 48.5 mmol) and potassium carbonate (13.4 g, 97.0 mmol) in CH3CN (200 ml). The mixture was refluxed under stirring for 21 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue was chromatographed on silica gel (eluting with 1.5% methanol/chloroform) to afford N-[3-(1,2,3,4-tetrahydro-1-naphthylamino)propyl]phthalimide (23.9 g, 74%): MS(ES+) m/e 335 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.84 (m, 2H), 7.71 (m, 2H), 7.39 (m, 1H), 7.13 (m, 2H), 7.06 (m, 1H), 3.81 (m, 3H), 2.81 (m, 2H), 2.71 (m, 2H), 2.00-1.85 (m, 4H), 1.72 (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 1.5% methanol/chloroform)

Sources & evidence

ORD record
ord-82b605a901f54fbb9f8efb1e5b7a8cbb
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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