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

HRID 1910615Notes

Reaction equation

HRID 1910615 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-607b18e516424ce9aa3f1613f40633fc
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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