Methanesulfonic Acid → 1,3-Bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl)benzoyl]-1-piperazinyl]propane dimethanesulfonate

HRID 1006237Notes

Reaction equation

HRID 1006237 reaction equation
[CH:1]([O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([C:13]2[CH:57]=[CH:56][C:16]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][N:28]4[CH2:33][CH2:32][N:31]([C:34](=[O:55])[C:35]5[CH:40]=[CH:39][C:38]([C:41]6[CH:46]=[C:45]([O:47][CH3:48])[C:44]([O:49][CH:50]([CH3:52])[CH3:51])=[C:43]([O:53][CH3:54])[CH:42]=6)=[CH:37][CH:36]=5)[CH2:30][CH2:29]4)[CH2:21][CH2:20]3)=[O:18])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[O:58][CH3:59])([CH3:3])[CH3:2].[CH3:60][S:61]([OH:64])(=[O:63])=[O:62].COC(C)(C)C>C(O)(C)C>[CH3:60][S:61]([OH:64])(=[O:63])=[O:62].[CH3:60][S:61]([OH:64])(=[O:63])=[O:62].[CH:50]([O:49][C:44]1[C:45]([O:47][CH3:48])=[CH:46][C:41]([C:38]2[CH:39]=[CH:40][C:35]([C:34]([N:31]3[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][CH2:25][N:22]4[CH2:23][CH2:24][N:19]([C:17](=[O:18])[C:16]5[CH:15]=[CH:14][C:13]([C:8]6[CH:7]=[C:6]([O:58][CH3:59])[C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[C:10]([O:11][CH3:12])[CH:9]=6)=[CH:57][CH:56]=5)[CH2:20][CH2:21]4)[CH2:29][CH2:30]3)=[O:55])=[CH:36][CH:37]=2)=[CH:42][C:43]=1[O:53][CH3:54])([CH3:51])[CH3:52]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 15413tert-Butyl methyl etherHCID 104407901,3-Bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl)benzoyl]-1-piperazinyl]propane

Product 1

HCID 226768581,3-Bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl)benzoyl]-1-piperazinyl]propane dimethanesulfonateYield 89.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 5.90 g (7.29 mmol) of 1,3-bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl) benzoyl]-l-piperazinyl]propane in isopropanol (90 mL) was heated to 50° C. and a solution of 1.41 g (14.7 mmol) of methanesulfonic acid in isopropanol (30 mL) was added. t-Butyl methyl ether (30 mL) was added and the mixture was stirred for 5 minutes at 50° C., for 30 minutes at room temperature, then for 30 minutes in an ice bath. Precipitates were collected by filtration and washed with t-butyl methyl ether to afford 6.54 g of 1,3-bis[4-[4-(4-isopropoxy-3,5-dimethoxyphenyl)benzoyl]-1-piperazinyl]propane dimethanesulfonate as a colorless crystalline powder (yield: 90a). mp: 235.5° C. (decomposed).

Workup

  1. waitfor 30 minutes in an ice bath
  2. customPrecipitates
  3. filtrationwere collected by filtration
  4. washwashed with t-butyl methyl ether

Sources & evidence

ORD record
ord-b2589c33429c4d97b208b64b24d5b853
Source dataset
uspto-grants-2004_09
Patent number
US06787653B2

Reaction notes

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