Hydrochloric Acid → 1,3-Bis[4-[4-(3,5-dimethoxy-4-propoxyphenyl) benzoyl)-1-piperazinyl]propane dihydrochloride

HRID 1006242Notes

Reaction equation

HRID 1006242 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[CH:59]=[CH:58][C:18]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][N:33]([C:36](=[O:57])[C:37]5[CH:42]=[CH:41][C:40]([C:43]6[CH:48]=[C:47]([O:49][CH3:50])[C:46]([O:51][CH2:52][CH2:53][CH3:54])=[C:45]([O:55][CH3:56])[CH:44]=6)=[CH:39][CH:38]=5)[CH2:32][CH2:31]4)[CH2:23][CH2:22]3)=[O:20])=[CH:17][CH:16]=2)[CH:6]=[C:7]([O:13][CH3:14])[C:8]=1[O:9][CH2:10][CH2:11][CH3:12].C(OCC)(=O)C.[ClH:66].C(OCC)C>CO>[ClH:66].[ClH:66].[CH3:50][O:49][C:47]1[CH:48]=[C:43]([C:40]2[CH:39]=[CH:38][C:37]([C:36]([N:33]3[CH2:34][CH2:35][N:30]([CH2:29][CH2:28][CH2:27][N:24]4[CH2:25][CH2:26][N:21]([C:19](=[O:20])[C:18]5[CH:58]=[CH:59][C:15]([C:5]6[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH2:10][CH2:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=6)=[CH:16][CH:17]=5)[CH2:22][CH2:23]4)[CH2:31][CH2:32]3)=[O:57])=[CH:42][CH:41]=2)[CH:44]=[C:45]([O:55][CH3:56])[C:46]=1[O:51][CH2:52][CH2:53][CH3:54]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 102599621,3-Bis[4-[4-(3,5-dimethoxy-4-propoxyphenyl) benzoyl]-1-piperazinyl]propane

Product 1

HCID 226768651,3-Bis[4-[4-(3,5-dimethoxy-4-propoxyphenyl) benzoyl)-1-piperazinyl]propane dihydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4.2 g (5.19 mmol) of 1,3-bis[4-[4-(3,5-dimethoxy-4-propoxyphenyl) benzoyl]-1-piperazinyl]propane in methanol (30 mL) stirred in an ice bath, was added 3.2 mL (13 mmol) of a 4.0 mol/L ethyl acetate solution of hydrogen chloride, and the mixture was concentrated under reduced pressure. Methanol (50 mL) was added and the mixture was concentrated under reduced pressure again. A suspension of the residue in methanol-chloroform (10:1, 44 mL) was stirred at 40° C. to give a homogeneous solution. Diethyl ether (10 mL) was added to the solution and the mixture was stirred at room temperature and at 0° C. Precipitates were collected by filtration and washed successively with methanol-diethyl ether (2:3) and diethyl ether to afford 3.92 g of 1,3-bis[4-[4-(3,5-dimethoxy-4-propoxyphenyl) benzoyl)-1-piperazinyl]propane dihydrochloride as a colorless crystalline powder (yield: 86%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionMethanol (50 mL) was added
  3. concentrationthe mixture was concentrated under reduced pressure again
  4. additionA suspension of the residue in methanol-chloroform (10:1, 44 mL)
  5. customto give a homogeneous solution
  6. stirringthe mixture was stirred at room temperature and at 0° C
  7. customPrecipitates
  8. filtrationwere collected by filtration
  9. washwashed successively with methanol-diethyl ether (2:3) and diethyl ether

Sources & evidence

ORD record
ord-8b25129524f4496a848ee70643f1c89c
Source dataset
uspto-grants-2004_09
Patent number
US06787653B2

Reaction notes

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