Hydrochloric Acid → 1,2,3,4-Tetrahydro-2-methyl-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine hydrochloride

HRID 2426057Notes

Reaction equation

HRID 2426057 reaction equation
[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[NH:12][C:13]1[CH:18]=[C:17]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:16]=[CH:15][C:14]=1[S:25]([CH3:28])(=[O:27])=[O:26].[ClH:29]>ClCCl.C(OCC)C>[ClH:29].[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[NH:12][C:13]1[CH:18]=[C:17]([N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[CH:16]=[CH:15][C:14]=1[S:25]([CH3:28])(=[O:27])=[O:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 587072671,2,3,4-tetrahydro-2-methyl-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine

Product 1

HCID 671475231,2,3,4-Tetrahydro-2-methyl-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-2-methyl-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine (70.0 mg, 0.18 mmol) in anhydrous dichloromethane (1.0 mL) was cooled to 0° C. and HCl (96 μL of a 1M solution in diethyl ether, 0.19 mmol) were added. The mixture was allowed to stir for 10 min. After removal of solvent by rotary evaporation the desired product was collected (82.0 mg, 100%). 1H NMR (400 MHz, CD3OD): δ 7.58 (d, 1H), 7.25 (t, 1H), 7.15 (m, 3H), 6.41 (d, 1H), 6.27 (s, 1H), 4.45 (d, 1H), 3.47 (m, 4H), 3.36 (m, 1H), 3.30 (m, 4H), 2.98 (s, 3H), 2.30 (m, 1H), 2.08 (m, 2H), 1.72 (m, 1H), 1.13 (d, 3H); MS (ESI) m/z: 400.2 (M++1).

Workup

  1. customAfter removal of solvent
  2. customby rotary evaporation the desired product
  3. customwas collected (82.0 mg, 100%)

Sources & evidence

ORD record
ord-69c44649c7de4e808c0949023feb00ed
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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