1-Butanol → HCID 21922925, compound

HRID 1272648Notes

Reaction equation

HRID 1272648 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.[NH2:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=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:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:32][CH:33]=2)[N:3]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 2337BenzocaineHCID 21923086HCID 21923086, compound

Product 1

HCID 21922925HCID 21922925, compoundYield 69.8%

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 158 mg of ethyl 4-amino-benzoate 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 two days 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 methylene chloride/ethyl acetate in a proportion of 90/10, 209 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 two days 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 methylene chloride/ethyl acetate in a proportion of 90/10

Sources & evidence

ORD record
ord-506858d53ee146a3854597194f126dd8
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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