Sodium Hydroxide → 1-[2-(Benzyloxy)ethyl]-4-(3-phenylpropyl)piperazine

HRID 1198394Notes

Reaction equation

HRID 1198394 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=O)[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:14][CH2:13]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1>[C:1]1([CH2:7][O:8][CH2:9][CH2:10][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:14][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19102668HCID 19102668, compound

Product 1

HCID 49130761-[2-(Benzyloxy)ethyl]-4-(3-phenylpropyl)piperazineYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-[(phenylmethoxy)acetyl]-4-(3-phenylpropionyl)piperazine (193 g) in tetrahydrofuran (967 ml) under a nitrogen atmosphere, was added a molar solution of borane-tetrahydrofuran complex solution in tetrahydrofuran (2.4 l) and the mixture was refluxed for 1 h. The residual borane reagent was destroyed by dropwise addition of 5N hydrochloric acid solution (430 ml) and the tetrahydrofuran was removed by distillation. The cooled reaction mixture was basified with sodium hydroxide solution, the product was extracted with ethyl acetate, and the solvents were evaporated in vacuo, after which 1-[2-(phenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (178 g) was obtained.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. customThe residual borane reagent was destroyed by dropwise addition of 5N hydrochloric acid solution (430 ml)
  3. customthe tetrahydrofuran was removed by distillation
  4. customThe cooled reaction mixture
  5. extractionthe product was extracted with ethyl acetate
  6. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-4fb6761620ca496699aad7a09d817ada
Source dataset
uspto-grants-1994_01
Patent number
US05281598

Reaction notes

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