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Water → 1-Carbomethoxy-4-[4,4-bis(p-fluorophenyl)butyl]-piperazine hydrochloride

HRID 542182
Notes
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Reaction equation

HRID 542182 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2].[Cl:11][CH2:12][CH2:13][CH2:14][CH:15]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+].O>C(O)C>[ClH:11].[C:1]([N:5]1[CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][CH:15]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 142729Methyl piperazine-1-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 202094811-Carbomethoxy-4-[4,4-bis(p-fluorophenyl)butyl]-piperazine hydrochlorideYield 17.3%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To a solution of 4.3 g (0.03 mole) 1-carbomethoxypiperazine in 10 ml of ethanol was added 10.0 g (0.036 mole) of 4-chloro-1,1-bis-(p-fluorophenyl)-butane and 5.0 g of sodium bicarbonate. The mixture was heated at reflux for 36 hours. 100 ml of water was added. The mixture was extracted twice with Et2O. The combined extracts were dried over sodium sulphate and concentrated. The residue was dissolved in ethanol-ether and the hydrochloride was precipitated with ethanolic HCl. The solid was collected by filtration and recrystallised from propan-2-ol to give 2.2 g of 1-carbomethoxy-4-[4,4-bis(p-fluorophenyl)butyl]-piperazine hydrochloride. Melting point 192°-193° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 36 hours
  3. extractionThe mixture was extracted twice with Et2O
  4. dry with materialThe combined extracts were dried over sodium sulphate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethanol-ether
  7. customthe hydrochloride was precipitated with ethanolic HCl
  8. filtrationThe solid was collected by filtration
  9. customrecrystallised from propan-2-ol

Sources & evidence

ORD record
ord-7c0001171b8048a3ad3c61c16d4fe6cc
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04656175

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes