Hydrochloric Acid → N-(1-(5-Chloro-2-methoxyphenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine hydrochloride

HRID 1910549Notes

Reaction equation

HRID 1910549 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:14]=[CH:13][C:12]=2[S:23]([CH3:26])(=[O:25])=[O:24])[CH3:9])[CH:7]=1.Cl>ClCCl.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)[CH:14]=[CH:13][C:12]=2[S:23]([CH3:26])(=[O:24])=[O:25])[CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11575438N-(1-(5-chloro-2-methoxyphenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine

Product 1

HCID 67147343N-(1-(5-Chloro-2-methoxyphenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine hydrochlorideYield 200%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(5-chloro-2-methoxyphenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine (15.0 mg, 0.04 mmol) in dichloromethane (1 mL) was added 10 mL of 1 M HCl in ether. The solution was allowed to stir for 1 h after which a precipitate formed. The solvent was removed by rotary evaporation to collect the title compound (16.0 mg, 0.04 mmol) in 100% yield. 1H NMR (400 MHz, CD3OD): δ 8.10 (s, 1H), 7.55 (s, 1H), 7.30 (d, 1H), 7.21 (q, 1H), 7.02 (d, 1H), 6.39 (d, 1H), 4.66 (m, 1H), 3.92 (s, 3H), 3.40 (m, 4H), 3.26 (m, 4H), 1.53 (d, 3H); MS (ESI) m/z: Calculated for C20H27ClN3O3S: 424.15; Observed: (M++1) [corresponding to the free base].

Workup

  1. customformed
  2. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-6651030c2fd04d7e813ae7d2b79e5d58
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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