1-Phenylpiperazine → HCID 71217379, compound

HRID 1887951Notes

Reaction equation

HRID 1887951 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:32])[C:7]([CH2:18][NH:19][C:20](=[O:31])OC3C=CC([N+]([O-])=O)=CC=3)=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[C:33]1([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:32])[C:7]([CH2:18][NH:19][C:20]([N:42]3[CH2:43][CH2:44][N:39]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:40][CH2:41]3)=[O:31])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 866757694-Nitrophenyl (7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamate2×

Product 1

HCID 71217379HCID 71217379, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 25 mL round-bottomed flask, 4-nitrophenyl (7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamate (intermediate M) (0.05 g, 0.111 mmol), 1-phenylpiperazine (18.0 mg, 0.111 mmol) and N,N-diisopropylethylamine (43.1 mg, 58.2 μA, 333 mmol) were combined with methylene chloride (5 mL). The reaction mixture was stirred at room temperature. The crude product was purified using preparative reverse-phase HPLC, giving 4-phenyl-piperazine-1-carboxylic acid (7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide MS calcd. for C27H26ClN4O2 [(M+H)+] 473.2, obsd. 473.0.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-14d811f9e78a4254818fcc0119d4579c
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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