Benzoyl chloride → HCID 12392227, compound

HRID 1973405Notes

Reaction equation

HRID 1973405 reaction equation
[OH:1][CH:2]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([NH2:10])[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[OH:1][CH:2]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([NH:10][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 12392203HCID 12392203, compound

Product 1

HCID 12392227HCID 12392227, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred slurry of 8.60 g (0.0334 mol) of 3-[1-hydroxy-2-(4aminopiperazin-1-yl)ethyl]indole in 50 ml. of chloroform is added 4.55 g (0.045 mol) of triethylamine. The mixture is cooled to 0° C. under a nitrogen atmosphere, and a solution of 5.64 g (0.040 mol) benzoyl chloride in 10 ml. of chloroform is introduced dropwise for 1 hour, while maintaining the reaction temperature of 0°-5° C. The resulting mixture is stirred at 0° C. for one hour, and at ambient temperature for another hour. The mixture is diluted with 150 ml. of chloroform and then 100 ml. of 10% sodium hydroxide. This mixture is stirred for 15 minutes and then filtered; the cake is washed well with water and dried to give a white solid. This product is recrystallized first from an ethanol and water mixture and then twice from DMF and water to give pure white crystals of 3-[1-hydroxy-2-(4-benzamidopiperazin-1-yl)ethyl]indole, m.p. 211°-213° C. dec. Analysis: Calculated for C21H24N4 02 : 69.21% C; 6.64% H; 15.37% N Found: 69.00% C; 6.60% H; 15.28% N.

Workup

  1. temperaturewhile maintaining the reaction temperature of 0°-5° C
  2. waitat ambient temperature for another hour
  3. additionThe mixture is diluted with 150 ml
  4. stirringThis mixture is stirred for 15 minutes
  5. filtrationfiltered
  6. washthe cake is washed well with water
  7. customdried
  8. customto give a white solid
  9. customThis product is recrystallized first from an ethanol and water mixture

Sources & evidence

ORD record
ord-3646edb40ab14eb2842518dafe59d070
Source dataset
uspto-grants-1976_12
Patent number
US03997539

Reaction notes

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