1-Iodononane → HCID 12052516, compound

HRID 1633532Notes

Reaction equation

HRID 1633532 reaction equation
[CH3:1][N:2]1[C@H:14]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=32)[CH2:4][CH2:3]1.[I:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CC(O)=O>[I-:15].[CH3:1][N:2]1[C@H:14]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][N+:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][C:13]=32)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 202751-IodononaneHCID 6336060HCID 6336060, compound

Product 1

HCID 12052516HCID 12052516, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of cis-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinoline (120 mg, 0.64 mmol) in AcOH (2 ml) was added 1-iodononane (488 mg, 1.92 mmol). The mixture was heated at reflux under nitrogen for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried. Evaporation of the solvent followed by titration with ether afforded 222 mg (79%) of cis-1-methyl-8-nonyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinolin-8-ium iodide (ACN) as a brown oil. 1H NMR (300 MHz, CDCl3) δ9.05 (1H, s, C9-H), 9.03 (1H, d, J6.0 Hz, C7-H), 7.81 (1H, d, J6.0 Hz, C6-H), 4.88 (2H, m. pyCH2), 3.47 (1H, d, J8.7 Hz, C9b-H), 2.36 (3H, s, NCH3), 1.60-3.10 (9H, m, CH2+CH), 2.00 (2H, m, pyCH2CH2), 1.10-1.50 (12H, m, 6×CH2), 0.83 (3H, t, J6.9 Hz, CH2CH3); 13C NMR (75 MHz, CDCl3) δ161.7, 143.4, 142.5, 139.2, 127.5, 63.5, 61.5, 55.9, 41.3, 35.9, 32.1, 32.0, 30.3, 29.5, 29.3, 29.2, 28.2, 27.6, 26.2, 22.8, 14.2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 3 days
  3. customAcOH was evaporated
  4. dissolutionthe residue was dissolved in CHCl3
  5. washThe mixture was washed with saturated aqueous NaHCO3, water and brine successively
  6. customdried
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d731958b104b433589fd0efb0078f7c6
Source dataset
uspto-grants-2003_01
Patent number
US06503922B2

Reaction notes

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