Methyl iodide → HCID 20298878, compound

HRID 1389247Notes

Reaction equation

HRID 1389247 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:23]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.CI>O1CCCC1.O>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([N:16]([CH3:23])[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 20298881HCID 20298881, compound

Product 1

HCID 20298878HCID 20298878, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.01 mole of N-(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)-4-pyridinamine in 100 milliliters of dry tetrahydrofuran is added at -10° C. to a solution of lithium diisopropylamide (prepared from 1.5 milliliters (0.01 mole) of diisopropylamine and butyl lithium in hexane (7.7 milliliters; 0.01 mole) at -20° C.) in 100 milliliters of tetrahydrofuran, in an atmosphere of nitrogen. The solution is stirred at room temperature for 30 minutes and then treated with 0.63 milliliters (0.01 mole) of methyl iodide and stirred at room temperature overnight. The solution is decomposed with 5 milliliters of water and evaporated and the residue is dissolved in propan-2-ol. Acidification with ethereal hydrogen chloride followed by careful addition of ether gives the title compound in hydrochloride form.

Workup

  1. stirringstirred at room temperature overnight
  2. customevaporated
  3. dissolutionthe residue is dissolved in propan-2-ol
  4. additionAcidification with ethereal hydrogen chloride followed by careful addition of ether

Sources & evidence

ORD record
ord-236a0df132964a09911e530b27d42f93
Source dataset
uspto-grants-1981_01
Patent number
US04243808

Reaction notes

Loading…