Hydrochloric Acid → N-(2-Methyl-1-phenylpropyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochloride

HRID 2425995Notes

Reaction equation

HRID 2425995 reaction equation
[ClH:1].[CH3:2][CH:3]([CH3:34])[CH:4]([NH:11][C:12]1[CH:13]=[C:14]([N:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)C.ClCCl>[ClH:1].[CH3:2][CH:3]([CH3:34])[CH:4]([NH:11][C:12]1[CH:13]=[C:14]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707253Tert-butyl 4-(3-(2-methyl-1-phenylpropylamino)-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 67147341N-(2-Methyl-1-phenylpropyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochlorideYield 53%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A saturated solution of HCl gas in anhydrous diethyl ether was added portion wise to a solution of tert-butyl 4-(3-(2-methyl-1-phenylpropylamino)-4-nitrophenyl)piperazine-1-carboxylate (145 mg, 0.32 mmol) in anhydrous dichloromethane (0.5 mL). The resulting mixture was allowed to stand at room temperature for 30 min, and conversion was monitored by LCMS. The solvent was concentrated down in vacuo and co-evaporated with diethyl ether to yield 60 mg (53%) of the title compound: 1H NMR (400 MHz, CD3OD): δ 8.04 (dd, 1H), 7.36-7.32 (m, 4H), 7.28-7.24 (m, 1H), 6.34 (br d, 1H), 5.89 (br s, 1H), 4.45 (br d, 1H), 3.50-3.20 (m, 8H), 2.18 (m, 1H), 1.09 (d, 3H), 0.98 (d, 3H). MS (ESI) m/z: Calculated: 354.26; Observed: 355.6 (M++1) [corresponding to the free base].

Workup

  1. concentrationThe solvent was concentrated down in vacuo and co-evaporated with diethyl ether

Sources & evidence

ORD record
ord-e3548a0675ee43dc807b1e2e1bc8ef9d
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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