Hydrochloric Acid → HCID 86664771, compound

HRID 1910574Notes

Reaction equation

HRID 1910574 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:13]2[C:14]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:15]([NH2:25])[CH:16]=[C:17]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:18]=2)[CH3:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[ClH:30]>ClCCl.C(OCC)C>[ClH:30].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:13]2[C:14]([S:26]([CH3:29])(=[O:27])=[O:28])=[C:15]([NH2:25])[CH:16]=[C:17]([N:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[CH:18]=2)[CH3:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86664772HCID 86664772, compound

Product 1

HCID 86664771HCID 86664771, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(3,5-dimethoxyphenyl)ethyl-2-(methylsulfonyl)-5-(piperazin-1-yl)-benzeneamine (500 mg, 1.19 mmol) in dichloromethane (5.0 mL) was added 1M solution of HCl in diethyl ether (25 mL). The reaction mixture was stirred for 3 h. The solvent was removed by rotary evaporation to afford the title compound (521 mg, 96% yield). 1H NMR (400 MHz, CD3OD): δ 7.55 (m, 1H), 6.57 (s, 3H), 6.36 (m, 1H), 5.49 (s, 1H), 4.61 (m, 1H), 3.75 (s, 6H), 3.41 (m, 4H), 3.25 (m, 4H), 3.18 (m, 2H), 3.21 (s, 3H), 1.55 (d, 3H); MS (ESI) m/z: Calculated for C21H30ClN3O4S: 455.16; Observed: 456.2 (M++1).

Workup

  1. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-cb1277a9835448a0a65560bc6e59d788
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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