Dichloromethane → 3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl methanesulfonate

HRID 2294141Notes

Reaction equation

HRID 2294141 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:11][CH2:10]1.C(Cl)Cl.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>C(N(CC)CC)C>[CH3:22][S:23]([O:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:11][CH2:10][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:14][CH2:13]1)(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 4109013-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-ol

Product 1

HCID 108061843-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-propanol (24 g, 95.87 mmol), prepared as in Example 10, in 25 mL of triethylamine and 300 mL of methylene chloride was cooled to approximately 0° C. and then methanesulfonyl chloride (8.8 mL) was added dropwise. The mixture was stirred at approximately 0° C. for 1 hour and then at room temperature for 0.5 hours. The mixture was poured into saturated sodium carbonate and stirred for 15 minutes. The organic phase was separated, washed with saturated sodium carbonate (2×150 mL), dried (MgSO4) and concentrated to give 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl methanesulfonate (21 g, 63.63 mmol).

Workup

  1. waitat room temperature for 0.5 hours
  2. stirringstirred for 15 minutes
  3. customThe organic phase was separated
  4. washwashed with saturated sodium carbonate (2×150 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-47bcbbe90e324b8a8821b5e288446cdd
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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