Hydrochloric Acid → N-(3-Chlorobenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide hydrochloride

HRID 704208Notes

Reaction equation

HRID 704208 reaction equation
[Cl:1]C1C=C(C=CC=1)CNC(C1C=CC2SC3C(=CC=CC=3)N(C(C)CN3CCCC3)C=2C=1)=S.[Cl:34][C:35]1[CH:36]=[C:37]([CH:64]=[CH:65][CH:66]=1)[CH2:38][NH:39][C:40]([C:42]1[CH:55]=[CH:54][C:53]2[S:52][C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([CH:56]([CH3:63])[CH2:57][N:58]3[CH2:62][CH2:61][CH2:60][CH2:59]3)[C:44]=2[CH:43]=1)=[O:41].Cl>C(O)(=O)C.C(#N)C.C(OCC)C>[ClH:1].[Cl:34][C:35]1[CH:36]=[C:37]([CH:64]=[CH:65][CH:66]=1)[CH2:38][NH:39][C:40]([C:42]1[CH:55]=[CH:54][C:53]2[S:52][C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([CH:56]([CH3:63])[CH2:57][N:58]3[CH2:59][CH2:60][CH2:61][CH2:62]3)[C:44]=2[CH:43]=1)=[O:41]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 15925380N-(3-chlorobenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamideHCID 53845975N-(3-chlorobenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 67922690N-(3-Chlorobenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide hydrochloride

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Working in a manner similar to that described below in Example 80, but starting with N-(3-chlorobenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide, L series (2 g) in acetic acid (60 cc) and with mercuric acetate (1.3 g), N-(3-chlorobenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (1.2 g) is obtained in the form of a yellow product of meringue-like consistency. This product is dissolved in acetonitrile (20 cc), and a 2.4 N solution (0.8 cc) of hydrochloric acid in ethyl ether is then added. The crystals are separated by filtration and dried under reduced pressure (5 mm Hg; 0.67 kPa) at 40° C. N-(3-Chlorobenzyl)-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide hydrochloride, L series (1.0 g) is obtained in the form of white crystals, m.p. 208° C.

Workup

  1. customL series (1.2 g) is obtained in the form of a yellow product of meringue-like consistency
  2. customThe crystals are separated by filtration
  3. customdried under reduced pressure (5 mm Hg; 0.67 kPa) at 40° C

Sources & evidence

ORD record
ord-37766b14bde74e98b979d539646f60c7
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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