Cyclobutylmethylamine → N-cyclobutylmethyl-10-[(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

HRID 1109542Notes

Reaction equation

HRID 1109542 reaction equation
Cl.[N:2]1([CH2:7][CH:8]([N:10]2[C:23]3[CH:22]=[C:21]([C:24](O)=[O:25])[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.[CH:27]1([CH2:31][NH2:32])[CH2:30][CH2:29][CH2:28]1>ClCCl>[CH:27]1([CH2:31][NH:32][C:24]([C:21]2[CH:20]=[CH:19][C:18]3[S:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH:8]([CH2:7][N:2]4[CH2:3][CH2:4][CH2:5][CH2:6]4)[CH3:9])[C:23]=3[CH:22]=2)=[O:25])[CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 409746CyclobutylmethylamineHCID 1453664010-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride

Product 1

HCID 15096214N-cyclobutylmethyl-10-[(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamideYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using a procedure similar to that described in Example 15, but starting with 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride (3.4 g) in dichloromethane (100 cc) and cyclobutylmethylamine (4.5 g), and after recrystallization in isopropyl ether, N-cyclobutylmethyl-10-[(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (1.7 g) is obtained in the form of white crystals, m.p. 133° C.

Workup

  1. customafter recrystallization in isopropyl ether

Sources & evidence

ORD record
ord-c065d544c9b34dc595841d7de44bb2dd
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

Loading…