Gramine → HCID 67713751, compound

HRID 1684519Notes

Reaction equation

HRID 1684519 reaction equation
CN([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][NH:15]1>C1(C)C=CC=CC=1>[NH:15]1[C:14]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:17][CH:16]1[CH2:4][C:5]1[C:9]2[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6890GramineHCID 422478Isoindoline

Product 1

HCID 67713751HCID 67713751, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To gramine (731 mgs, 4.2 mmol) in dry PhMe (20 ml) was added 1,2-dihydroisoindole (prepared as in Org. Syn., Coll. Vol. V, p. 406) (500 mgs, 4.2 mmol) and the reaction refluxed for 6 h. The solvent was evaporated, the residue triturated with PhMe and the resultant solid recrystallised from PhMe to yield the title compound (550 mgs, 52%). M.p. 168°-170° C.; (Found: C, 80.44; H, 6.46; N, 10.98. C17H16N2.0.25H2O) requires C, 80.76; H, 6.38; N, 11.08%). δH (CDCl3) 4.00 (4H, s, 2×isoindolinyl CH2), 4.11 (2H, s, NCH2Ar), 7.08-7.23 (7H, m, ArH), 7.36 (1H, d, J 7.9 Hz, ArH), 7.77 (1H, d, J 7.9 Hz, ArH), 8.18 (1H, brs, NH); m/z (CI+, NH3) 249 (M+1)+.

Workup

  1. temperaturethe reaction refluxed for 6 h
  2. customThe solvent was evaporated
  3. customthe residue triturated with PhMe
  4. customthe resultant solid recrystallised from PhMe

Sources & evidence

ORD record
ord-be28cfcf9e7f45ceac37ad21ac3714ae
Source dataset
uspto-grants-1997_06
Patent number
US05641787

Reaction notes

Loading…