Benzoyl chloride → HCID 12392234, compound

HRID 1973407Notes

Reaction equation

HRID 1973407 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[NH:12][C:11]=2[CH3:23])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[OH-].[Na+]>C(OCC)C.C(Cl)(Cl)Cl>[C:31]([NH:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[NH:12][C:11]=2[CH3:23])[CH2:4][CH2:3]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 123922024-[2-(5,6-Dimethoxy-2-methyl-1H-indol-3-yl)ethyl]piperazin-1-amine

Product 1

HCID 12392234HCID 12392234, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent2×

Procedure

A stirred mixture of 7.92 g (0.025 mol) of 3-[2-(4-aminopiperazin-1-yl)ethyl]-5,6-dimethoxy-2-methylindole and 3.54 g (0.035 mol) of triethylamine in 75 ml. of chloroform is cooled to -5° C., with the exclusion of moisture. Then a solution of 4.20 g (0.03 mol) of benzoyl chloride in 6 ml. of chloroform is added dropwise over a 30 minute span, while maintaining a temperature of 0°-5° C. After total addition, the mixture is stirred at ambient temperature for two hours. Then 50 ml. of 10% sodium hydroxide is added, followed by 50 ml. of ethyl ether to promote crystallization. After stirring for 15minutes, another 100 ml. of ethyl ether is added to improve crystallization form. The product is filtered, washed well with water, then ethyl ether and dried. This crystalline product is recrystallized twice from DMF and water mixture to give pure needles of 3-[2-(4 -benzamidopiperazin-1-yl)ethyl]-5,6-dimethoxy-2-methylindole, m.p. 128°-131° C. Analysis: Calculated for C24H30N4O3 : 68.22% C; 7.16% H; 13.26% N Found: 68.03% C; 7.14% H; 13.12% N.

Workup

  1. temperaturewhile maintaining a temperature of 0°-5° C
  2. additionAfter total addition
  3. customcrystallization
  4. stirringAfter stirring for 15minutes
  5. additionof ethyl ether is added
  6. customcrystallization form
  7. filtrationThe product is filtered
  8. washwashed well with water
  9. dry with materialethyl ether and dried
  10. customThis crystalline product is recrystallized twice from DMF and water mixture

Sources & evidence

ORD record
ord-f5f28ac159b140cbbe2913487755c680
Source dataset
uspto-grants-1976_12
Patent number
US03997539

Reaction notes

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