Hydrochloric Acid → N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-(4-methylpiperazin-1-yl)-2-(methylsulfonyl)benzenamine hydrochloride

HRID 2426072Notes

Reaction equation

HRID 2426072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:30][CH3:31])[C:5]([O:28][CH3:29])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[CH:14]=[CH:13][C:12]=2[S:24]([CH3:27])(=[O:26])=[O:25])[CH3:9])[CH:7]=1.Cl>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([O:30][CH3:31])[C:5]([O:28][CH3:29])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)[CH:14]=[CH:13][C:12]=2[S:24]([CH3:27])(=[O:25])=[O:26])[CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707275N-(1-(5-chloro-2,3-dimethoxyphenyl)ethyl)-5-(4-methylpiperazin-1-yl)-2-(methylsulfonyl)benzenamine

Product 1

HCID 67147329N-(1-(5-Chloro-2,3-dimethoxyphenyl)ethyl)-5-(4-methylpiperazin-1-yl)-2-(methylsulfonyl)benzenamine hydrochlorideYield 180%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(5-chloro-2,3-dimethoxyphenyl)ethyl)-5-(4-methylpiperazin-1-yl)-2-(methylsulfonyl)benzenamine (45.1 mg, 0.10 mmol) in dichloromethane (2 mL) was added 0.06 mL (0.13 mmol) of 2 M HCl in diethyl ether. The solution was allowed to stir for 15 minutes and the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and triturated with diethyl ether. The solvent was removed by rotary evaporation to collect the title compound (43.0 mg, 0.09 mmol) in 89.6% yield. 1H NMR (400 MHz, CD3OD): δ 7.51 (d, 1H), 6.92 (m, 2H), 6.36 (d, 1H), 6.10 (s, 1H), 4.94 (m, 1H), 3.92 (m, 4H), 3.89 (s, 3H), 3.86 (s, 3H), 3.49 (m, 2H), 3.11 (m, 2H), 3.04 (s, 3H), 2.90 (s, 3H), 1.56 (d, 3H); MS (ESI) m/z: 468.0 (M++1).

Workup

  1. customthe solvent was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in dichloromethane
  3. customtriturated with diethyl ether
  4. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-9b3995ebf6454dbba4b72602a403a863
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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