Fumaric Acid → 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide fumarate

HRID 728716Notes

Reaction equation

HRID 728716 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH2:9]([N:11]([CH2:36][CH3:37])[CH2:12][CH:13]([N:15]1[C:28]2[CH:27]=[C:26]([C:29]([NH:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[O:30])[CH:25]=[CH:24][C:23]=2[S:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:14])[CH3:10]>CC(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH2:36]([N:11]([CH2:9][CH3:10])[CH2:12][CH:13]([N:15]1[C:28]2[CH:27]=[C:26]([C:29]([NH:31][CH2:32][CH:33]([CH3:35])[CH3:34])=[O:30])[CH:25]=[CH:24][C:23]=2[S:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:14])[CH3:37]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 1453657110-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide

Product 1

HCID 1453657210-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide fumarateYield 80.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Fumaric acid (0.18 g) dissolved in 2-propanol (7.5 cc) under reflux is added to a solution of 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide (0.62 g) in boiling 2-propanol (7.5 cc). The mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and the residue is stirred in isopropyl ether (50 cc). The solid is separated by filtration on sintered glass, washed with isopropyl ether (10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) to give 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarboxamide fumarate (0.64 g), m.p. 110° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  3. customThe solid is separated by filtration on sintered glass
  4. washwashed with isopropyl ether (10 cc)
  5. customdried under reduced pressure (5 mm Hg; 0.7 kPa)

Sources & evidence

ORD record
ord-de8258936fa747c49401092510a7fdb3
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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