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Sodium Hydroxide → 1-(2-Chloro-3-methylphenyl)-4-(3,4,5-trimethoxybenzyl)piperazine

HRID 1738805
Notes
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Reaction equation

HRID 1738805 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:24][CH2:23][N:22]([C:25]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=2)=O)[CH2:21][CH2:20]1.[OH-].[Na+]>C(OCC)C.O1CCCC1>[Cl:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N:19]1[CH2:20][CH2:21][N:22]([CH2:25][C:27]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=2)[CH2:23][CH2:24]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 15434661[4-(2-Chloro-3-methylphenyl)piperazine-1-yl]-(3,4,5-trimethoxyphenyl)methanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 102938041-(2-Chloro-3-methylphenyl)-4-(3,4,5-trimethoxybenzyl)piperazineYield 85.1%

Reagents, catalysts & solvents

2
HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of aluminum chloride (0.279 g, 2.09 mmol) in anhydrous diethyl ether (20 mL) is added dropwise to a suspension of lithium aluminum hydride (0.238 g, 6.27 mmol) in anhydrous tetrahydrofuran (20 mL) at 0° C. and stirred for 0.5 hour. To this mixture is added dropwise a solution of [4-(2-chloro-3-methylphenyl)piperazine-1-yl]-(3,4,5-trimethoxy-phenyl)methanone (2.12 g, 5.23 mmol) in anhydrous tetrahydrofuran (20 mL). The suspension is stirred for 2 hours at 0° C., followed by dropwise addition of 2N sodium hydroxide. The mixture is filtered through Celite and concentrated in vacuo. The resulting product is purified by MPLC on silica gel eluting with 40% ethyl acetate/hexane to give 1.74 g of the title compound as a white solid; mp 112-113° C.

Workup

  1. stirringThe suspension is stirred for 2 hours at 0° C.
  2. filtrationThe mixture is filtered through Celite
  3. concentrationconcentrated in vacuo
  4. customThe resulting product is purified by MPLC on silica gel eluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f0b67009c3ca46a29ac3c7874d219f19
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05965560

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes