Hydrochloric Acid → HCID 14156731, compound

HRID 579976Notes

Reaction equation

HRID 579976 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[CH2:17][CH2:18][N:10]([C:11]=23)[C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]=2[NH:7]1.[CH3:24][N:25]=[C:26]=[O:27].[ClH:28]>C1(C)C=CC=CC=1.CCOCC.CCOCC.CO>[ClH:28].[CH3:23][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[CH2:17][CH2:18][N:10]([C:11]=23)[C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]=2[N:7]1[C:26]([NH:25][CH3:24])=[O:27]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 12228Methyl IsocyanateHCID 12685803HCID 12685803, compound

Product 1

HCID 14156731HCID 14156731, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

To a solution of 6.26 g of N,N-dimethyl-1,2,6,7-tetrahydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-propanamine in 125 ml of dry toluene was added 2.36 ml of methyl isocyanate, via syringe, under nitrogen. After stirring the mixture overnight at room temperature it was diluted with ether (500 ml) and the resulting solution was washed with water (2×250 ml) and saturated sodium chloride solution and thereafter dried over anhydrous sodium sulfate. Filtration and concentration in vacuo afforded a foam weighing 6.72 g. This material was dissolved in 5:1 ether/methanol solution (approx. 150 ml) and treated dropwise with hydrogen chloride-saturated ether solution with stirring. Crude salt formed as an insoluble oil on the side wall of the flask. After a few minutes of stirring, the liquid phase was decanted and fresh ether used to triturate the crude salt to a solid. Filtration and drying in vacuo afforded 6.72 g of solid. This material was combined with some crude salt prepared in an analogous manner and dissolved in 25 ml of boiling isopropanol. The hot solution was gravity-filtered, allowed to cool and stand at room temperature for a few minutes and then was refrigerated overnight. The recrystallized salt was filtered, washed twice with cold isopropanol, and ether and dried in vacuo to afford 4.7 g of crystalline solid, m.p. 233°-235° C.

Workup

  1. washthe resulting solution was washed with water (2×250 ml) and saturated sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration in vacuo
  4. customafforded a foam
  5. stirringwith stirring
  6. customCrude salt formed as an insoluble oil on the side wall of the flask
  7. stirringAfter a few minutes of stirring
  8. customthe liquid phase was decanted
  9. customto triturate the crude salt to a solid
  10. filtrationFiltration
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-a5e19e92eff34e77948aa819a3436400
Source dataset
uspto-grants-1988_06
Patent number
US04751223

Reaction notes

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