Water → 1,2,3,4-tetrahydro-2-methyl-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amine

HRID 1910616Notes

Reaction equation

HRID 1910616 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([S:20]([CH3:23])(=[O:22])=[O:21])=[C:6]([NH:8][CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH:10]2[CH3:19])[CH:7]=1.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)C(C)C)(C)C.O>CN(C)C=O>[CH3:19][CH:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]1[NH:8][C:6]1[CH:7]=[C:2]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:3]=[CH:4][C:5]=1[S:20]([CH3:23])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 58707335HCID 58707335, compound

Product 1

HCID 587072671,2,3,4-tetrahydro-2-methyl-N-(2-(methylsulfonyl)-5-(piperazin-1-yl)phenyl)naphthalen-1-amineYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(5-fluoro-2-(methylsulfonyl)phenyl)-1,2,3,4-tetrahydro-2-methylnaphthalen-1-amine (63.3 mg, 0.19 mmol), piperazine (328 mg, 3.79 mmol) and N,N-diisopropylethylamine (0.34 mL, 1.99 mmol) in N,N-dimethylformamide (3 mL) was stirred at 110° C. for 16 h. The reaction mixture was cooled down, poured over 10 mL of water and extracted with diethyl ether. After evaporation of solvent the crude product was purified by silica chromatography (10% methanol in dichloromethane) to yield 70 mg (92%) of desired product. 1H NMR (400 MHz, CDCl3): δ 7.61 (d, 1H), 7.29 (m, 1H), 7.14 (m, 3H), 6.46 (d, 1H), 6.27 (dd, 1H), 12.2 (d, 1H), 4.28 (t, 1H), 3.29 (m, 1H), 3.20 (m, 4H), 3.01 (m, 1H), 2.96 (m, 4H), 2.88 (s, 3H), 2.30-1.70 (m, 4H), 1.12 (d, 3H); MS (ESI) m/z: 400.1 (M++1).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. extractionextracted with diethyl ether
  3. customAfter evaporation of solvent the crude product
  4. customwas purified by silica chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-382fbaa68c7449e19d70cc013dacfbe9
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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