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N,N,N',N'-Tetramethylethylenediamine → 4-Benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 10177
Notes
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Reaction equation

HRID 10177 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCN(C)C.C([Li])(CC)C.Br[CH2:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH:13]1[CH2:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 703202-BromomethylnaphthaleneHCID 584330Tert-butyl 4-benzylpiperazine-1-carboxylateHCID 178418400CID 53628100

Product 1

HCID 210410814-Benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
2×

Conditions

Temperature
-70 °C

Procedure

To a solution of 4-benzyl-piperazine-1-carboxylic acid tert-butyl ester (2 g) in diethylether (35 mL) was added tetramethylethylenediamine (1.4 mL). The resulting mixture was cooled to −70° C. and sec-butyllithium (7 mL of a 1.3 M solution) was added dropwise, after complete addition the solution was slowly warmed to −10° C., at which temperature the mixture was stirred for one hour. Subsequently, the mixture was recooled to −70° C.; then a solution of 2-(bromomethyl)naphthalene (2 g) in diethylether was added dropwise and stirring continued at −70° C. was continued for one hour. The resulting mixture was stirred and allowed to come to room temperature overnight, then partitioned between saturated ammonium chloride (aq) and ethyl acetate. The organic layer was dried over magnesium sulphate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 99/1) to afford 4-benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester as an oil. 0.8 g (27 %) Rf 0.47 (CH2Cl2/MeOH 99/1), MH+ 417.

Workup

  1. additionafter complete addition the solution
  2. temperaturewas slowly warmed to −10° C., at which temperature the mixture
  3. customwas recooled to −70° C.
  4. stirringstirring
  5. customcontinued at −70° C.
  6. waitwas continued for one hour
  7. stirringThe resulting mixture was stirred
  8. waitto come to room temperature overnight
  9. custompartitioned between saturated ammonium chloride (aq) and ethyl acetate
  10. dry with materialThe organic layer was dried over magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH 99/1)

Sources & evidence

ORD record
ord-4894c875297347dab46acb76b5f533c2
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094779B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes