Acetic Anhydride → HCID 14370158, compound

HRID 2291665Notes

Reaction equation

HRID 2291665 reaction equation
[CH:1]12[CH2:8][CH2:7][CH2:6][CH:5]1[CH:4]([C:9]([OH:11])=O)[CH2:3][CH:2]2[C:12]([OH:14])=O.C(OC(=O)C)(=O)C.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[CH2:29][CH2:28]1>O>[N:34]1[CH:35]=[CH:36][CH:37]=[N:38][C:33]=1[N:30]1[CH2:31][CH2:32][N:27]([CH2:26][CH2:25][CH2:24][CH2:23][N:22]2[C:12](=[O:14])[CH:2]3[CH2:3][CH:4]([CH:5]4[CH2:6][CH2:7][CH2:8][CH:1]43)[C:9]2=[O:11])[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 128407054-(2-Pyrimidinyl)-1-piperazinebutanamineHCID 14370157HCID 14370157, compound

Product 1

HCID 14370158HCID 14370158, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bicyclo[3.3.0]-octane-2,4-dicarboxylic acid (1.6 g., 8.1 mmole) was converted to the anhydride by refluxing for three hours in 100 ml. of acetic anhydride. The excess reagent was removed in vacuo. Two hundred fifty (250) ml. of xylene was added along with 1.9 g. (8.1 mmole) of 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine. The mixture was refluxed under nitrogen for 48 hours with water removal via a Dean-Stark trap. The solvent was then removed in vacuo and the residue filtered through 75 g. of silica gel with 2% ethanol/chloroform as eluent. Removal of solvent and recrystallization of the residue from isopropanol with the addition of 4N isopropanolic HCl, followed by a second recrystallization from isopropanol, gave 750 mg. of white solid title compound as hydrochloride, one quarter hydrate, m.p. 188°-189° C.

Workup

  1. temperatureby refluxing for three hours in 100 ml
  2. customThe excess reagent was removed in vacuo
  3. additionof xylene was added along with 1.9 g
  4. customThe solvent was then removed in vacuo
  5. filtrationthe residue filtered through 75 g
  6. customRemoval of solvent and recrystallization of the residue from isopropanol
  7. additionwith the addition of 4N isopropanolic HCl
  8. customfollowed by a second recrystallization from isopropanol
  9. customgave 750 mg

Sources & evidence

ORD record
ord-303e330911ed4fe98d3b63b3b6c8f9a0
Source dataset
uspto-grants-1989_01
Patent number
US04797488

Reaction notes

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