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

HRID 1109541Notes

Reaction equation

HRID 1109541 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

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 3283Diethyl EtherSolvent

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 treated with a 3N solution (10 cc) of ethereal hydrogen chloride and diluted with acetone (100 cc) and ethyl ether (100 cc), then filtered. After seeding, the yellow filtrate allows 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 yellow crystals, m.p. 215°-217° C.

Workup

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

Sources & evidence

ORD record
ord-6918bc7a7a7844b8b6080474949de735
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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