Dichloromethane → HCID 14156367, compound

HRID 1253263Notes

Reaction equation

HRID 1253263 reaction equation
[CH:1]12[C:9](=[O:10])[O:8][C:6](=O)[CH:3]([CH2:4][CH2:5]1)[CH2:2]2.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:18][CH2:17]1.C(Cl)Cl.C1(C)C(C)=CC=CC=1>O>[F:31][C:28]([F:29])([F:30])[C:24]1[CH:23]=[C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:11]3[C:6](=[O:8])[CH:3]4[CH2:2][CH:1]([CH2:5][CH2:4]4)[C:9]3=[O:10])[CH2:21][CH2:20]2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7237O-XyleneHCID 2397991,3-Cyclopentanedicarboxylic anhydrideHCID 111624114-[3-(Trifluoromethyl)phenyl]-1-piperazinebutanamine

Product 1

HCID 14156367HCID 14156367, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Cyclopentane dicarboxylic anhydride (2.2 g., 15 mmole) and 1-(4-aminobutyl)-4-[3-(trifluoromethyl)phenyl]piperazine (4.5 g., 15 mmole) were combined in 300 ml. of methylene chloride and stirred for 30 minutes at room temperature. The solvent was replaced with 200 ml. of xylene and the mixture was refluxed for 48 hours with water removal via a Dean-Stark trap. The solvent was removed in vacuum and the residue filtered through 75 g. of silica gel with 2% ethanol/chloroform as eluent. The product was concentrated in vacuum and crystallized from 50 ml. of isopropanol with the addition of 5 ml. of 4N isopropanolic HCl. A second recrystallization from ethanol gave 2.7 g. of the title compound as the hydrochloride, quarter hydrate; m.p. 208°-209° C.

Workup

  1. customThe solvent was removed in vacuum
  2. filtrationthe residue filtered through 75 g
  3. concentrationThe product was concentrated in vacuum
  4. customcrystallized from 50 ml
  5. additionof isopropanol with the addition of 5 ml
  6. customA second recrystallization from ethanol
  7. customgave 2.7 g

Sources & evidence

ORD record
ord-b8dcc0fa628b48a8a28e77b66b881c38
Source dataset
uspto-grants-1988_05
Patent number
US04748240

Reaction notes

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