Hydrochloric Acid → HCID 20289599, compound

HRID 1414049Notes

Reaction equation

HRID 1414049 reaction equation
[ClH:1].Cl.[Cl:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:9]3=[N:10][C:6]=2[CH:5]=1.I[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[Na+].[Na+].Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)C>[ClH:3].[ClH:1].[CH2:19]([N:13]1[CH2:12][CH2:11][C:9]2=[N:10][C:6]3[CH:5]=[C:4]([Cl:3])[CH:17]=[CH:16][C:7]=3[N:8]2[CH2:15][CH2:14]1)[CH2:20][CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 336431-IodopropaneHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 13015898HCID 13015898, compound

Product 1

HCID 20289599HCID 20289599, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1.1 g. (5 mmole) of 8-chloro-2,3,4,5-tetrahydro-1H-1,4-diazepino[17-a]benzimidazole prepared in Example 1 above, 0.85 g. (5 mmole) 1-iodopropane, and 0.75 g. (7.5 mmole) of sodium carbonate in 100 ml. of 95% ethanol is refluxed 72 hours. After removing the solvent in vacuo, the residue is chromatographed over silica gel, eluting with hexane/chloroform saturated with ammonia (1:4). The product obtained is dissolved in absolute ethanol and acidified with ethanolic hydrochloric acid. The crystals which separate are filtered and dried to afford 0.41 g. (25%) of the dihydrochloride salt: m.p. 271°-274° C.

Workup

  1. customAfter removing the solvent in vacuo
  2. customthe residue is chromatographed over silica gel
  3. washeluting with hexane/chloroform saturated with ammonia (1:4)
  4. customThe product obtained
  5. customThe crystals which separate
  6. filtrationare filtered
  7. customdried
  8. customto afford 0.41 g

Sources & evidence

ORD record
ord-4b5378c326894e7d9ded0341f3ed1e25
Source dataset
uspto-grants-1981_02
Patent number
US04252816

Reaction notes

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