3-(1-Piperazinyl)propanamide → HCID 128684, compound

HRID 2118483Notes

Reaction equation

HRID 2118483 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]3[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:8]=3[CH:9](Cl)[CH2:10][C:4]=2[CH:3]=1.[N:19]1([CH2:25][CH2:26][C:27]([NH2:29])=[O:28])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]3[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:8]=3[CH:9]([N:22]3[CH2:21][CH2:20][N:19]([CH2:25][CH2:26][C:27]([NH2:29])=[O:28])[CH2:24][CH2:23]3)[CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 5446973-(1-Piperazinyl)propanamideHCID 12232369HCID 12232369, compound

Product 1

HCID 128684HCID 128684, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2,10-dichloro-7-fluoro-10,11-dihydrodibenzo(b,f)-thiepin (2.8 g), 3-(1-piperazinyl)propionamide (3.2 g) and chloroform (10 ml) is refluxed with stirring for 8 hours. The solvent is than evaporated under reduced pressure, and the residue is extracted by shaking with a two-phase system consisting of benzene (30 ml) and a solution of methanesulfonic acid (4 g) in water (50 ml). The clear aqueous solution is separated and then made alkaline with aqueous ammonia (10 ml). The so-formed suspension of the amorphous base is diluted with ethanol (100 ml), and the mixture is briefly warmed to boiling. The resultant clear solution is then allowed to crystallize at room temperature for 6 hours. The crystalline product is separated, washed with a small amount of ethanol, and then dried in vacuo. The obtained base (2.35 g, 60% of theory) melts at 179°-182° C.; it can be purified by crystallization from ethanol to give the title compound having a m.p. of 182°-184° C. and which is identical with the product of the preceding example 1.

Workup

  1. temperatureis refluxed
  2. customthan evaporated under reduced pressure
  3. extractionthe residue is extracted
  4. stirringby shaking with a two-phase system
  5. customThe clear aqueous solution is separated
  6. additionThe so-formed suspension of the amorphous base
  7. additionis diluted with ethanol (100 ml)
  8. temperaturethe mixture is briefly warmed to boiling
  9. customto crystallize at room temperature for 6 hours
  10. customThe crystalline product is separated
  11. washwashed with a small amount of ethanol
  12. customdried in vacuo
  13. customit can be purified by crystallization from ethanol

Sources & evidence

ORD record
ord-f1715414a7be4906bdb636d7589ad38c
Source dataset
uspto-grants-1987_07
Patent number
US04678788

Reaction notes

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