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Triethylamine → 1-(Benzyloxycarbonyl)-3-(2,3-dimethoxybenzyl)piperazine

HRID 584218
Notes
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Reaction equation

HRID 584218 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:15]=1[CH2:16][CH:17]1[CH2:22][NH:21][CH2:20][CH2:19][NH:18]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl.O>[CH2:1]([O:8][C:9]([N:21]1[CH2:20][CH2:19][NH:18][CH:17]([CH2:16][C:15]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:14]=2[O:13][CH3:12])[CH2:22]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 22342949HCID 22342949, compound

Product 1

HCID 223427101-(Benzyloxycarbonyl)-3-(2,3-dimethoxybenzyl)piperazineYield 53.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent3×

Procedure

A solution of benzyloxycarbonyl chloride (0.59 g) in dichloromethane (3.0 ml) was added dropwise to a solution of 2-(2,3-dimethoxybenzyl)piperazine (0.91 g) and triethylamine (0.64 ml) in dichloromethane (18 ml) below 5° C. over 5 minutes under ice-cooling, and the reaction mixture was stirred at the same temperature for 15 minutes. After 2 hours of stirring at room temperature, the mixture was poured into a mixed solvent of water (40 ml) and dichloromethane (25 ml) and the whole was adjusted to pH 9 with aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (20 g) using a mixed solvent of dichloromethane and methanol (40:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give colorless oil of 1-(benzyloxycarbonyl)-3-(2,3-dimethoxybenzyl)piperazine (0.68 g).

Workup

  1. temperaturecooling
  2. stirringAfter 2 hours of stirring at room temperature
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (20 g)
  8. additionThe fractions containing the objective compound
  9. customwere collected
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-328a69c68dc94231a7094a2e031bd54d
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06924278B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes