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(2-Nitrophenyl)methanamine → N-(2-nitrobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

HRID 704244
Notes
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Reaction equation

HRID 704244 reaction equation
Cl.[N:2]1([CH2:7][CH:8]([N:10]2[C:23]3[CH:22]=[C:21]([C:24](Cl)=[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.[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33])([O-:29])=[O:28]>ClCCl>[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH:33][C:24]([C:21]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:8]([CH3:9])[CH2:7][N:2]3[CH2:6][CH2:5][CH2:4][CH2:3]3)[C:23]=2[CH:22]=1)=[O:25])([O-:29])=[O:28]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 423893(2-Nitrophenyl)methanamineHCID 2007488610-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride

Product 1

HCID 20074883N-(2-nitrobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamideYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By working in a manner similar to that described in Example 103, but starting with 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride (2.5 g) in dichloromethane (50 cc) and with 2-nitrobenzylamine (2.1 g), N-(2-nitrobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (1.1 g) is obtained, after recrystallization in isopropyl ether, in the form of yellow crystals, m.p. 95° C.

Sources & evidence

ORD record
ord-6cd4e6c7cb5a4544b493d586f7f756f4
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04985419

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes