Dimethylformamide → 1-[(5-chloro-1-benzothien-3-yl)methyl]-4-(6-methyl-2-pyridinyl)Piperazine

HRID 1768335Notes

Reaction equation

HRID 1768335 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1.[CH3:13][C:14]1[N:19]=[C:18]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=1.CN(C)C=O.ClCCl>C(#N)C>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]2[S:5][CH:4]=[C:3]([CH2:2][N:23]3[CH2:24][CH2:25][N:20]([C:18]4[CH:17]=[CH:16][CH:15]=[C:14]([CH3:13])[N:19]=4)[CH2:21][CH2:22]3)[C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 27369461-(6-Methylpyridin-2-yl)piperazineHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiophene

Product 1

HCID 100212701-[(5-chloro-1-benzothien-3-yl)methyl]-4-(6-methyl-2-pyridinyl)Piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

3-(Bromomethyl)-5-chloro-1-benzothiophene (1 mmol, maybridge chemical) and 1-(6-methyl-2-pyridinyl)piperazine (1 mmol) were combined in 2 mL of acetonitrile and 1 mL of dimethylformamide and stirred at 25° C. for 5 minutes. The mixture was heated briefly to dissolve any solids and allowed to cool to 25° C. The mixture was monitored by thin layer chromatography until disappearance of starting residue. The mixture was poured into dichloromethane and washed with dilute aqueous ammonium hydroxide. The organic phase was dried over sodium sulfate, filtered, and the filtrate concentrated. The residue was purified by flash chromatography with dichloromethane/methanol/saturated aqueous ammonia to provide the title compound. 1H NMR (d6-DMSO, 300 MHz) δ 2.29 (s, 3H), 3.31 (m, 6H), 3.45 (m, 2H), 3.74 (s, 2H), 6.48 (d, 1H, J=7.5 Hz), 6.57 (d, 1H, J=7.8 Hz), 7.38–7.42 (m, 2H), 7.71 (s, 1H), 8.02 (d, 1H, J=7.8 Hz), 8.06 (d, 1H, J=1.5 Hz); MS (DCI/NH3) m/z 358.1 (M+H)+.

Workup

  1. temperatureThe mixture was heated briefly
  2. dissolutionto dissolve any solids
  3. washwashed with dilute aqueous ammonium hydroxide
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customThe residue was purified by flash chromatography with dichloromethane/methanol/saturated aqueous ammonia

Sources & evidence

ORD record
ord-3deec8033dc74962a2cbb9f1876b06e7
Source dataset
uspto-grants-2007_06
Patent number
US07235661B2

Reaction notes

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