Fumaric Acid → N-Cyclobutylmethyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide fumarate

HRID 704216Notes

Reaction equation

HRID 704216 reaction equation
[CH:1]1([CH2:5][NH:6][C:7]([C:9]2[CH:22]=[CH:21][C:20]3[S:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH:23]([CH3:30])[CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[C:11]=3[CH:10]=2)=[O:8])[CH2:4][CH2:3][CH2:2]1.[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35]>CC(O)C.C(OC(C)C)(C)C.CC(C)=O>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35].[CH:1]1([CH2:5][NH:6][C:7]([C:9]2[CH:22]=[CH:21][C:20]3[S:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH:23]([CH3:30])[CH2:24][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29]4)[C:11]=3[CH:10]=2)=[O:8])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 444972Fumaric AcidHCID 15096214N-cyclobutylmethyl-10-[(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

Product 1

HCID 20074895N-Cyclobutylmethyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide fumarate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3776IsopropanolSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A boiling solution of N-cyclobutylmethyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (1.7 g) in 2-propanol (17 cc) containing fumaric acid (0.47 g) is allowed to cool. The mixture is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give a residue which is taken up in isopropyl ether (100 cc). The mixture is stirred for 1 hour at 20° C. The suspension obtained is filtered and the solid is washed with isopropyl ether (2×5 cc) and dried under reduced pressure (5 mm Hg; 0.67 kPa) at 50° C. to give a cream-coloured powder, which is dissolved in acetone (25 cc) under reflux. Crystallization develops. The mixture is stirred for 16 hours at 20° C. and the crystals are drained and dried under reduced pressure (5 mm Hg; 0.67 kPa) at 50° C. N-Cyclobutylmethyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide fumarate, L series (0.64 g) is thereby obtained in the form of cream-coloured crystals, m.p., 126°-128° C.

Workup

  1. temperatureto cool
  2. concentrationThe mixture is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  3. customto give a residue which
  4. customThe suspension obtained
  5. filtrationis filtered
  6. washthe solid is washed with isopropyl ether (2×5 cc)
  7. customdried under reduced pressure (5 mm Hg; 0.67 kPa) at 50° C.
  8. customto give a cream-coloured powder, which
  9. temperatureunder reflux
  10. customCrystallization
  11. stirringThe mixture is stirred for 16 hours at 20° C.
  12. customdried under reduced pressure (5 mm Hg; 0.67 kPa) at 50° C

Sources & evidence

ORD record
ord-9dfcf0b31dca47e39ee451bfe9d9b191
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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