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Methyl bromoacetate → [4-(3-Methoxy-phenyl)-piperidin-1-yl]-acetic Acid Methyl Ester

HRID 902644
Notes
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Reaction equation

HRID 902644 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:15][O:16][C:17](=[O:20])[CH2:18]Br.C(N(C(C)C)CC)(C)C>CO>[CH3:15][O:16][C:17](=[O:20])[CH2:18][N:12]1[CH2:13][CH2:14][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:10][CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 107028904-(3-Methoxyphenyl)piperidine

Product 1

HCID 69252936[4-(3-Methoxy-phenyl)-piperidin-1-yl]-acetic Acid Methyl EsterYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(3-Methoxy-phenyl)-piperidine (0.8 g, 4.2 mmol), methylbromoacetate (1.28 g, 8.38 mmol), diisopropylethylamine (3.7 mL, 21 mmol) and MeOH (40 mL) was refluxed for 3 h. The reaction mixture was concentrated in vacuo, and the residue was partitioned between water and EtOAc and extracted. The organic layer was washed with water, brine, dried and concentrated in vacuo to give the title compound as an oil (1.0 g, 91% yield). MS(ESI) 264.2 (M+H+)

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. extractionextracted
  5. washThe organic layer was washed with water, brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ae15fdc37d54ce7b0490ad22c5ef0c8
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07365085B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes