Hydrochloric Acid → HCID 9848922, compound

HRID 1779339Notes

Reaction equation

HRID 1779339 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[C:10]([C:16]([O:18][CH3:19])=[O:17])[NH:11]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:20]1([C:27](=[O:38])[CH:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][CH2:30]Cl)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:18][C:16]([C:10]1[NH:11][C:12]2[C:8]([CH:9]=1)=[C:7]([N:1]1[CH2:6][CH2:5][N:4]([CH2:30][CH2:29][CH:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:27]([N:20]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:38])[CH2:3][CH2:2]1)[CH:15]=[CH:14][CH:13]=2)=[O:17]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 152860154-Chloro-1-(hexahydro-1H-azepin-1-yl)-2-phenyl-1-butanoneHCID 19955417HCID 19955417, compound

Product 1

HCID 9848922HCID 9848922, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

The product of Example 4 (1.30 g, 0.005 mol), 1-azepan-1-yl-4-chloro-2-phenylbutan-1-one (1.50 g, 0.005 mol), triethylamine (0.79 g, 0.0079 mol), and potassium iodide (0.2 g) were suspended in anhydrous dimethyl formamide (30 ml), stirred under argon for 3 h at 100° C., and poured into dilute potassium carbonate (300 ml). The mixture was extracted into ether (3×100 ml) and treated with excess dilute aqueous hydrogen chloride. The precipitate was filtered, washed with ether (3×100 ml), taken up into dilute sodium hydroxide solution (100 ml), and extracted into ether (3×100 ml). The extracts were dried (MgSO4), and evaporated in vacuo to give a yellow crystalline glass. Purification by chromatography [alumina; ethyl acetate-hexane (2:3)] gave the product free base. The dihydrochloride salt of the product (1.35 g) was precipated as a colourless solid by the addition of ethereal hydrogen chloride to a solution of the free base in ethyl acetate, m.p. 152°-168° C. (Found: C, 57.4; H, 7.45; N, 8.7. C30H38N4O3. 2HCl.3H2O requires C, 57.2; H, 7.4; N, 8.9%).

Workup

  1. extractionThe mixture was extracted into ether (3×100 ml)
  2. additiontreated with excess dilute aqueous hydrogen chloride
  3. filtrationThe precipitate was filtered
  4. washwashed with ether (3×100 ml)
  5. extractionextracted into ether (3×100 ml)
  6. dry with materialThe extracts were dried (MgSO4)
  7. customevaporated in vacuo
  8. customto give a yellow crystalline glass
  9. customPurification by chromatography [alumina; ethyl acetate-hexane (2:3)]
  10. customgave the product free base

Sources & evidence

ORD record
ord-b841de32a40e4358997a75ba9055e859
Source dataset
uspto-grants-1997_05
Patent number
US05627177

Reaction notes

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