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Sodium Hydroxide → 1-[(6-Bromopyridin-3-yl)methyl]-4-ethylpiperazine

HRID 2264359
Notes
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Reaction equation

HRID 2264359 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[Br:9][C:10]1[N:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[Br:9][C:10]1[N:15]=[CH:14][C:13]([CH2:16][N:6]2[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)=[CH:12][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 791961-EthylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 866428861-[(6-Bromopyridin-3-yl)methyl]-4-ethylpiperazine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

Add neat 1-ethylpiperazine (221.44 mL) to a mixture of 6-bromo-pyridine-3-carbaldehyde (300 g) and DCM (5000 mL). Then, add sodium triacetoxyborohydride (372.09 g) in portions and stir at RT for 12 h. Add DCM (1000 mL) and aqueous solution of sodium hydroxide 2 N (1500 mL). Separate the layers and extract twice the aqueous layer with DCM (600 mL). Combine the organic layers and remove the solvent under vacuum, add EA and evaporate to afford 451.3 g of the title compound. MS (ES+): m/z=285 (M+H)+.

Workup

  1. customSeparate the layers
  2. extractionextract twice the aqueous layer with DCM (600 mL)
  3. customCombine the organic layers and remove the solvent under vacuum
  4. additionadd EA
  5. customevaporate

Sources & evidence

ORD record
ord-6dbbec81435b4a2383206b4611f3a310
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07855211B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes