HCID 18694136, compound → HCID 131720892, compound

HRID 399917Notes

Reaction equation

HRID 399917 reaction equation
[O:1]1[C:6]2[C:7]3[CH2:13][CH2:12][CH2:11][C:8]=3[CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH2:19].[ClH:20].CS[C:23]1[NH:24][CH:25]=[CH:26][N:27]=1>C(O)C>[OH2:1].[ClH:20].[ClH:20].[NH:27]1[CH2:26][CH2:25][N:24]=[C:23]1[NH:19][CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH:2]1[CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][C:8]3[CH2:11][CH2:12][CH2:13][C:7]=3[C:6]=2[O:1]1.[NH:27]1[CH2:26][CH2:25][N:24]=[C:23]1[NH:19][CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH:2]1[CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][C:8]3[CH2:11][CH2:12][CH2:13][C:7]=3[C:6]=2[O:1]1.[ClH:20].[ClH:20]

Participants

4

Reactant 2

HCID 18694136HCID 18694136, compoundHCID 18694166HCID 18694166, compound

Product 1

HCID 131720892HCID 131720892, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate (15-a) (0.02 mol) and 2-methylthioimidazole monohydrochloride (0.02 mol) in ethanol (100 ml) was stirred and refluxed for 16 hours. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/(CH3OH/NH3) 90/9/1). The pure fractions were collected and the solvent was evaporated. The residue was dissolved in 2-propanol and converted into the hydrochloric acid salt (1:2) with HCl/2-propanol. The salt was filtered off and dried, yielding 2.4 g of (±)-N-(4,5-dihydro-1H-imidazol-2-yl)-N'-[(2,3,4,7,8,9-hexahydro cyclopenta[h]-1-benzopyran-2-yl)methyl]-1,3-propanediamine dihydrochloride hemihydrate; mp. 189.7° C. (comp. 9-a).

Workup

  1. temperaturerefluxed for 16 hours
  2. customThe solvent was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/(CH3OH/NH3) 90/9/1)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in 2-propanol
  7. filtrationThe salt was filtered off
  8. customdried

Sources & evidence

ORD record
ord-d0bf0848a5a3403fa45a003629f6624b
Source dataset
uspto-grants-1998_10
Patent number
US05824682

Reaction notes

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