Triethylamine → Methyl [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate

HRID 2119361Notes

Reaction equation

HRID 2119361 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:24][C:25]([O:27][CH3:28])=[O:26].CCN(CC)CC>CC#N>[C:17]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:12][CH2:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 234410351-(3,3-Diphenyipropyl)homopiperazine

Product 1

HCID 54512635Methyl [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetateYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3,3-Diphenylpropyl)homopiperazine (2.0 g, 6.79 mmol) was dissolved in CH3CN (60 mL) and treated with methyl bromoacetate (1.56 g, 10.18 mmol) and Et3N (1.42 mL, 10.18 mmol). The mixture was refluxed for 18 h and subsequently concentrated in vacuo. The residue was subjected to flash silica gel column chromatography (eluent: CH2Cl2/MeOH, 96/4, v/v) to give Methyl [4-(3,3-diphenylpropyl)homopiperazine-1-yl]acetate (1.93 g) in 78% yield, TLC Rf=0.53 (10% CH3OH—CH2Cl2); RPLC tR=4.71 min (>85%), 220 nm (Method A); ESI/MS m/e 367.1 (M++H, C23H30N2O2).

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. concentrationsubsequently concentrated in vacuo

Sources & evidence

ORD record
ord-44238c78e700416589ccad05256a96a0
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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