Hydrochloric Acid → N-(1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine hydrochloride

HRID 1910610Notes

Reaction equation

HRID 1910610 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[S:26]([CH3:29])(=[O:28])=[O:27])[CH3:12])[C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.Cl>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[S:26]([CH3:29])(=[O:28])=[O:27])[CH3:12])[C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707264N-(1-(5-chlorobenzo[d][1,3]dioxol-7-yl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine

Product 1

HCID 67147530N-(1-(5-Chlorobenzo[d][1,3]dioxol-7-yl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(1-(5-chlorobenzo[d][1,3]dioxol-7-yl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine (15.0 mg, 0.03 mmol) in anhydrous dichloromethane (0.5 mL) was cooled to 0° C. and HCl (34 μL of a 1M solution in diethyl ether, 0.03 mmol) were added. The mixture was allowed to stir for 30 min. The solvent was removed by rotary evaporation and co-evaporated with hexanes to precipitate the salt. After removal of solvent by rotary evaporation the desired product was collected (16 mg, 99%). 1H NMR (400 MHz, CD3OD): δ 7.55 (d, 1H), 6.92 (d, 1H), 6.78 (d, 1H), 6.41 (dd, 1H), 6.06 (m 1H), 5.99 (s, 1H), 4.69 (m, 1H), 3.44 (m, 4H), 3.26 (m, 4H), 3.06 (s, 3H), 1.59 (d, 3H); MS (ESI) m/z: 438.2.0 (M++1).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customto precipitate the salt
  3. customAfter removal of solvent
  4. customby rotary evaporation the desired product
  5. customwas collected (16 mg, 99%)

Sources & evidence

ORD record
ord-1690cccdb0b94dfd9fe9e12b145bd22c
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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