Diisopropylethylamine → HCID 10113365, compound

HRID 1006413Notes

Reaction equation

HRID 1006413 reaction equation
[C:1]1([S:11]([N:14]2[C:22]3[C:17](=[C:18]([NH2:23])[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]Cl.C(N(C(C)C)CC)(C)C>ClC1C=CC=CC=1>[C:1]1([S:11]([N:14]2[C:22]3[C:17](=[C:18]([N:23]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 11347838HCID 11347838, compound

Product 1

HCID 10113365HCID 10113365, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 461 mg (1.43 mmole) 1-(naphthalene-1-sulfonyl)-1H-indol-4-ylamine, 255 mg (1.43 mmole) bis(2-chloroethyl)amine hydrochloride, and 0.5 mL diisopropylethylamine in 5 mL chlorobenzene was heated under reflux. After 4 hours, 0.25 mL diisopropylethylamine was added and heating under reflux was continued for 15 hours. The mixture was partitioned between 25 mL ethyl acetate and 10 mL 5% sodium hydroxide. The organic phase was washed with 5 mL saturated sodium chloride solution, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to low pressure column chromatography over silica gel 230-400 mesh eluting with 8% methanol in chloroform. 1-(Naphthalene-1-sulfonyl)-4-piperazin-1-yl-1H-indole (1) was isolated as the hydrochloride salt from ethyl acetate/ether, 54 mg, M+H=392.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureheating
  4. temperatureunder reflux
  5. waitwas continued for 15 hours
  6. customThe mixture was partitioned between 25 mL ethyl acetate and 10 mL 5% sodium hydroxide
  7. washThe organic phase was washed with 5 mL saturated sodium chloride solution
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated under reduced pressure
  10. washeluting with 8% methanol in chloroform

Sources & evidence

ORD record
ord-634d46da63ba43748422c8bdf5e7554f
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Reaction notes

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