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Acetone → 10-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride

HRID 704238
Notes
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Reaction equation

HRID 704238 reaction equation
[ClH:1].[N:2]1([CH2:7][CH:8]([N:10]2[C:23]3[CH:22]=C(C#N)[CH:20]=[CH:19][C:18]=3[S:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-:26].[K+].Cl.C[C:30]([CH3:32])=[O:31]>C(OCC)C>[ClH:1].[N:2]1([CH2:7][CH:8]([N:10]2[C:23]3[CH:22]=[C:32]([C:30]([OH:26])=[O:31])[CH:20]=[CH:19][C:18]=3[S:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1902054310-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile hydrochloride

Product 1

HCID 1453664010-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Procedure

10-[(2RS)-1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile hydrochloride (3.72 g) is added to a solution of potassium hydroxide (1.7 g) in glycol (20 cc), and the mixture is stirred for 5 hours under reflux. After cooling, the yellow solution obtained is traeted with a 3N ethereal solution (10 cc) of hydrochloric acid, and diluted with acetone (100 cc) and ethyl ether (100 cc) and then filtered. The yellow filtrate, after priming, gives rise to the crystallization of a product, which is drained, washed with ethyl ether (2×10 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. 10-[(2RS)-1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride (3.5 g) is thereby obtained in the form of pale yellow crystals, m.p. 215°-217° C.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customthe yellow solution obtained
  4. filtrationfiltered
  5. customThe yellow filtrate, after priming, gives rise
  6. customto the crystallization of a product, which
  7. washwashed with ethyl ether (2×10 cc)
  8. customdried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C

Sources & evidence

ORD record
ord-6e575cacd2934a42b2707d859b388d67
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04985419

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes