Acetic Acid → 1-(4-Bromo-2-methoxyphenyl)-4-methylpiperazine

HRID 2384939Notes

Reaction equation

HRID 2384939 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[C:4]([O:14][CH3:15])[CH:3]=1.[C:16](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:16])[CH2:12][CH2:13]2)=[C:4]([O:14][CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 689488831-(4-Bromo-2-methoxyphenyl)piperazine

Product 1

HCID 593927241-(4-Bromo-2-methoxyphenyl)-4-methylpiperazineYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1-(4-bromo-2-methoxy-phenyl)-piperazine (7.0 g, 25.8 mmol) and acetic acid (5.9 mL, 103.2 mmol) in methanol (500 mL) and add aqueous formaldehyde (37%, 5.3 mL). After 5 min, add sodium cyanoborohydride (4.05 g, 64.5 mmol) and stir the mixture at room temperature overnight. Concentrate the reaction mixture in vacuo and partition between dichloromethane (200 mL) and 1 N sodium hydroxide (200 mL). Separate the organic portion and extract the aqueous portion with dichloromethane (2×100 mL). Dry the combined organics (Na2SO4), filter, and concentrate in vacuo to afford 7.1 g (96%) of the title compound. MS/ES m/z (79Br) 285.0 [M+H]−.

Workup

  1. concentrationConcentrate the reaction mixture in vacuo
  2. custompartition between dichloromethane (200 mL) and 1 N sodium hydroxide (200 mL)
  3. customSeparate the organic portion
  4. extractionextract the aqueous portion with dichloromethane (2×100 mL)
  5. dry with materialDry the combined organics (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-2f75e811028747f1af9b39dbb10074b3
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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