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

HRID 2426058Notes

Reaction equation

HRID 2426058 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-2a4f96302cb04dab817b04c37d754818
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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