1-Butanol → HCID 21923026, compound

HRID 1272645Notes

Reaction equation

HRID 1272645 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:4](Cl)[N:3]=1.C(O)CCC.[I:22][C:23]1[CH:24]=[C:25]([CH2:29][NH2:30])[CH:26]=[CH:27][CH:28]=1>C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:4]([NH:30][CH2:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([I:22])[CH:24]=2)[N:3]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 970123-IodobenzylamineHCID 21923086HCID 21923086, compound

Product 1

HCID 21923026HCID 21923026, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The operation is carried out as in Stage 2 of Example 3 starting from 200 mg of the product obtained in Stage 1 of Example 3 and 4 ml of butanol and using 0.123 ml of 3-iodo-benzenemethanamine in place of the benzylamine. Agitation is carried out at ambient temperature then the reaction medium is taken to a temperature of 80 to 85° C. for 22 hours, left to return to ambient temperature, diluted with 4 ml of isopropanol, left for three hours at a temperature of approximately 0° C., followed by separating, washing with 10 ml of isopropanol and drying at a temperature of approximately 50° C. After purification on silica eluting with cyclohexane/ethyl acetate/ methylene chloride in a proportion of 70/15/15, 235 mg of expected product is obtained in the form of white crystals.

Workup

  1. customis carried out at ambient temperature
  2. waitleft
  3. customto return to ambient temperature
  4. waitleft for three hours at a temperature of approximately 0° C.
  5. customby separating
  6. washwashing with 10 ml of isopropanol
  7. customdrying at a temperature of approximately 50° C
  8. customAfter purification on silica eluting with cyclohexane/ethyl acetate/ methylene chloride in a proportion of 70/15/15

Sources & evidence

ORD record
ord-d23d7c5603a14092863fb1e020c7e1f4
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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