Water → (S)-1,4-dibenzyl-2-vinylpiperazine

HRID 131391Notes

Reaction equation

HRID 131391 reaction equation
C(O)(=O)C(C1C=CC=CC=1)O.[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][C@@H:20]1[CH:32]=[CH2:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[OH-].[Na+]>CC(OC)(C)C>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][C@@H:20]1[CH:32]=[CH2:33])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69215334(s)-1,4-Dibenzyl-2-vinyl-piperazine mandelic acid salt

Product 1

HCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazineYield 99.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-vinyl-piperazine mandelic acid salt (200.0 g, 0.450 mol), water (1 L), and 5N sodium hydroxide (112.5 mL, 0.562 mol) and stir at ambient temperature for 15 minutes. Add MTBE (1 L) and stir at ambient temperature for 1 hour. Layer separate and wash the organics with water (2×1 L). Dry the organics over sodium sulfate, filter and concentrate in vacuo to afford 131.2 g of the title compound as an oil (99.7%). 1H NMR (500 MHz, DMSO-d6) δ 2.00 (bt, 1H), 2.07 (d, 2H), 2.56 (m, 1H), 2.58 (d, 2H), 2.84 (t, 1H), 3.02 (d, 1H), 3.49 (s, 2H), 3.91 (d, 1H), 5.15 (d, 1H), 5.25 (d, 1H), 5.81 (m, 1H), 7.27 (m, 10H). MS (ES+) M+H calcd for C20H24N2 292.43; found 293.10.

Workup

  1. customLayer separate
  2. washwash the organics with water (2×1 L)
  3. dry with materialDry the organics over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-2c24091a62b3424e8e1cf2377cd188d0
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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