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

HRID 1109543Notes

Reaction equation

HRID 1109543 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+].C[C:29]([CH3:31])=[O:30]>>[ClH:1].[N:2]1([CH2:7][CH:8]([N:10]2[C:23]3[CH:22]=[C:31]([C:29]([OH:26])=[O:30])[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

4

Reactant 3

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

Product 1

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

Procedure

10-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile hydrochloride, L series (5 g) is added to a solution of potassium hydroxide (1.75 g) in glycol (30 cc), and the mixture is stirred for 4 hours under reflux. After cooling, the yellow solution obtained is diluted with acetone (75 cc) and a 3N solution (5 cc) of hydrochloric acid in ethyl ether, filtered and diluted again with acetone (75 cc) and a 3N solution (5 cc) of hydrochloric acid in ethyl ether. After seeding, crystallization is allowed to take place for 15 hours at a temperature in the region of 5° C. The solid obtained is drained, washed with ethyl ether (10 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. 10-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride, L series (2.9 g), is thereby obtained in the form of a light yellow solid, m.p. 200° -210° C. (melts forming a paste).

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customthe yellow solution obtained
  4. filtrationa 3N solution (5 cc) of hydrochloric acid in ethyl ether, filtered
  5. additiondiluted again with acetone (75 cc)
  6. customcrystallization
  7. customfor 15 hours
  8. customin the region of 5° C
  9. customThe solid obtained
  10. washwashed with ethyl ether (10 cc)
  11. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-7861a301c718402f86370f033e448136
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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