Acetic Acid → HCID 12052522, compound

HRID 1633535Notes

Reaction equation

HRID 1633535 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][CH2:24][CH2:25][CH3:26].[CH3:27]C(O)=O>>[I-:15].[CH2:26]([N+:11]1[CH:10]=[CH:9][C:8]2[CH2:7][CH2:6][C@@H:5]3[CH2:4][CH2:3][N:2]([CH3:1])[C@@H:14]3[C:13]=2[CH:12]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:27]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 20276Undecane, 1-iodo-HCID 6336060HCID 6336060, compound

Product 1

HCID 12052522HCID 12052522, compoundYield 66%

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-iodoundecane (569 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 205 mg (66%) of cis-8-dodecyl-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinolin-8-ium iodide (ACDD) as a brown oil. 1H NMR (300 MHz, CDCl3) δ9.08 (1H, s, C9-H), 9.02 (1H, d, J6.3 Hz, C7-H), 7.79 (1H, d, J6.3 Hz, C6-H), 4.90 (2H, m. pyCH2), 3.48 (1H, d, J8.4 Hz, C9b-H), 2.36 (3H, s, NCH3), 1.50-3.10 (9H, m, CH2+CH), 2.00 (2H, m, pyCH2CH2), 1.10-1.40 (18H, m, 9×CH2), 0.85 (3H, t, J6.9 Hz, CH2CH3); 13C NMR (75 MHz, CDCl3) δ161.5, 143.3, 142.5, 138.8, 127.5, 63.1, 61.0, 55.7, 41.0, 35.6, 32.0, 31.9, 30.0, 29.6×2, 29.5, 29.4, 29.3, 29.1, 28.1, 27.3, 26.0, 22.7, 14.1.

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-d334cc3ff7e448e890afdc45fd65cd71
Source dataset
uspto-grants-2003_01
Patent number
US06503922B2

Reaction notes

Loading…