4-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amine → 3-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-9-thia-3-azabicyclo[3.3.1]nonane-2,4-dione

HRID 1253267Notes

Reaction equation

HRID 1253267 reaction equation
[S:1]1[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:2]1[CH2:3][CH2:4][CH2:5]2)=O.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[N:27][CH:26]=[C:25]([Cl:29])[N:24]=2)[CH2:19][CH2:18]1>C(Cl)Cl>[Cl:29][C:25]1[N:24]=[C:23]([N:20]2[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:12]3[C:7](=[O:9])[CH:6]4[S:1][CH:2]([CH2:3][CH2:4][CH2:5]4)[C:10]3=[O:11])[CH2:22][CH2:21]2)[CH:28]=[N:27][CH:26]=1

Participants

4

Reactant 2

HCID 140865264-[4-(6-Chloropyrazin-2-yl)piperazin-1-yl]butan-1-amineHCID 54010570Tetrahydrothiopyran-2,6-dicarboxylic anhydride

Product 1

HCID 141563753-[4-[4-(6-Chloro-2-pyrazinyl)-1-piperazinyl]butyl]-9-thia-3-azabicyclo[3.3.1]nonane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tetrahydrothiopyran-2,6-dicarboxylic anhydride (3.7 g., 21 mmole) and 1-(4-aminobutyl)-4-(6-chloro-2-pyrazinyl)piperazine (5.63 g., 21 mmole) were combined in 200 ml. of methylene chloride and stirred for 30 minutes at room temperature. The solvent was removed in vacuum and 200 ml. of toluene added. The mixture was refluxed for 48 hours with water removal via a Dean-Stark trap. Upon cooling, the reaction was concentrated to an oil and this was dissolved in 2% ethanol/chloroform and filtered through silica gel. The fractions which contained the product were concentrated in vacuum and the resulting residue was recrystallized from isopropyl alcohol with the addition of 4N isopropanolic HCl. 0.6 Grams of the title compound was obtained as the hydrochloride, hydrate; m.p. 248°-250° C.

Workup

  1. customThe solvent was removed in vacuum and 200 ml
  2. additionof toluene added
  3. temperatureThe mixture was refluxed for 48 hours with water removal via a Dean-Stark trap
  4. temperatureUpon cooling
  5. concentrationthe reaction was concentrated to an oil
  6. dissolutionthis was dissolved in 2% ethanol/chloroform
  7. filtrationfiltered through silica gel
  8. concentrationwere concentrated in vacuum
  9. customthe resulting residue was recrystallized from isopropyl alcohol with the addition of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-a0286dc6efa043949ddfecc8185664ec
Source dataset
uspto-grants-1988_05
Patent number
US04748240

Reaction notes

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