Hydrochloric Acid → 1,2,3,4-Tetrahydro-6,7-dimethoxy-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine hydrochloride

HRID 1910596Notes

Reaction equation

HRID 1910596 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([NH:15][C:16]1[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=1[S:28]([CH3:31])(=[O:30])=[O:29])[CH2:8][CH2:7][CH2:6]2.[ClH:32]>ClCCl.C(OCC)C>[ClH:32].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([NH:15][C:16]1[CH:21]=[C:20]([N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)[CH:19]=[CH:18][C:17]=1[S:28]([CH3:31])(=[O:30])=[O:29])[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 587073311,2,3,4-tetrahydro-6,7-dimethoxy-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine

Product 1

HCID 671473041,2,3,4-Tetrahydro-6,7-dimethoxy-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-6,7-dimethoxy-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine (20.0 mg, 0.05 mmol) in dichloromethane (2 mL) at 0° C. was added 29 μL of 2 M HCl in diethyl ether. The solution was allowed to stir for 10 minutes after which a precipitate formed. The solvent was removed by rotary evaporation to collect the title compound (25.0 mg, 0.05 mmol) in 100% yield. 1H NMR (400 MHz, CD3OD): δ 7.54 (d, 1H), 6.73 (s, 1H), 6.65 (s, 1H), 6.51 (dd, 1H), 6.43 (d, 1H), 6.38 (m, 1H), 5.90 (m, 1H), 3.81 (s, 3H), 3.79 (s, 3H), 3.54 (m, 4H), 3.34 (m, 4H), 3.02 (s, 3H), 2.69 (m, 2H), 2.25 (m, 2H); MS (ESI) m/z: 446.4 (M++1).

Workup

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

Sources & evidence

ORD record
ord-0baa88bfb6014279a0fd01abe45c4e3f
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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