1-Iodooctane → HCID 12052514, compound

HRID 1633531Notes

Reaction equation

HRID 1633531 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][CH3:23]>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][CH3:23])=[CH:12][C:13]=32)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 123801-IodooctaneHCID 6336060HCID 6336060, compound

Product 1

HCID 12052514HCID 12052514, compoundYield 68.3%

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 (100 mg, 0.53 mmol) in AcOH (2 ml) was added 1-iodooctane (383 mg, 1.59 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 155 mg (68%) of cis-1-methyl-8-octyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinolin-8-ium iodide (ACO) as a brown oil. 1H NMR (300 MHz, CDCl3) δ9.16 (1H, s, C9-H), 9.03 (1H, d, J6.0 Hz, C7-H), 7.82 (1H, d, J6.0 Hz, C6-H), 4.86 (2H, m. pyCH2), 3.66 (1H, d, J8.4 Hz, C9b-H), 2.43 (3H, s, NCH3), 1.55-3.20 (9H, m, CH2+CH), 1.99 (2H, m, pyCH2CH2), 1.00-1.50 (10H, m, 5×CH2), 0.81 (3H, t, J6.9 Hz, CH2CH3); 13C NMR (75 MHz, CDCl3) δ161.8, 143.5, 142.5, 138.2, 127.6, 63.4, 61.4, 55.8, 41.2, 35.8, 32.1, 31.8, 30.0, 29.2×2, 27.8, 27.6, 26.2, 22.7, 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-6959d3619e2c4da9bfe5924b46e15dee
Source dataset
uspto-grants-2003_01
Patent number
US06503922B2

Reaction notes

Loading…