Methanol → Sodium [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate

HRID 2119362Notes

Reaction equation

HRID 2119362 reaction equation
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]([O:20]C)=[O:19])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[OH-].[Na+:31]>O1CCOCC1>[C:22]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]([O-:20])=[O:19])[CH2:12][CH2:11]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1.[Na+:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 54512635Methyl [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate

Product 1

HCID 23718564Sodium [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetateYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate (0.327 g, 0.89 mmol) was dissolved in a mixture of dioxane (3.1 mL). MeOH (1.1 mL) and 4N NaOH (0.22 mL). After stirring for 30 min. 5 more drops of 4N NaOH were added and stirring was, continued until hydrolysis of the methyl ester was complete. The mixture was concentrated in vacuo and the residue subjected to flash silica gel column chromatography (eluent: CH2Cl2/MeOH, 1/1, v/v) to give sodium [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate (0.278 g) in 88% yield, TLC Rf=0.22 (10% CH3OH—CH2Cl2); RPLC tR=1.98 min (>85%), 220 nm (Method B); ESI/MS m/e 353.3 (M++H, C22H29N2O2).

Workup

  1. stirringstirring
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-1ea48a530a694e87b7bf4e27565d6156
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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