(S)-(1,4-dibenzyl-piperazin-2-yl)-acetaldehyde → (S)-2-(1,4-Dibenzyl-piperazin-2-yl)-1-phenyl-ethanol

HRID 1350525Notes

Reaction equation

HRID 1350525 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][C@@H:16]1[CH2:28][CH:29]=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH2:8]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH:16]1[CH2:28][C@@H:29]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:30])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 59732114(S)-(1,4-dibenzyl-piperazin-2-yl)-acetaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 69489665(S)-2-(1,4-Dibenzyl-piperazin-2-yl)-1-phenyl-ethanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Add phenyllithium (11.3 mL, 20.4 mmol, 1.8 M in cyclohexane-ether) dropwise to a −78° C. solution of (S)-(1,4-dibenzyl-piperazin-2-yl)-acetaldehyde (4.2 g, 13.6 mmol) in THF (60 mL). Stir 30 min at −78° C. and 4 h at ambient temperature. Add ice, brine, and extract with ether. Wash the extracts with brine, dry with sodium sulfate, filter and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (1%–4%) as the eluent to give 3.98 g (76%) of the title compound: mass spectrum (ion spray): m/z=387 (M+1). HR-MS calculated for C26H31N2O: 387.2436. Found 387.2442.

Workup

  1. extractionAdd ice, brine, and extract with ether
  2. washWash the extracts with brine
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate the filtrate
  6. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-e629c85a0a0641eea8f03cd9fb7f5aaa
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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