Hydrochloric Acid → 1-Benzhydryl-4-(3-methyloxetan-3-yl)piperazine

HRID 921685Notes

Reaction equation

HRID 921685 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2([CH2:24]S(C3C=CC=CC=3)(=O)=O)[CH2:23][O:22][CH2:21]2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].Cl>CO.C1COCC1>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2([CH3:24])[CH2:21][O:22][CH2:23]2)[CH2:16][CH2:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 867085541-Benzhydryl-4-(3-((phenylsulfonyl)methyl)oxetan-3-yl)piperazine

Product 1

HCID 867085551-Benzhydryl-4-(3-methyloxetan-3-yl)piperazineYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-benzhydryl-4-(3-((phenylsulfonyl)methyl)oxetan-3-yl)piperazine (2.49 g, 5.38 mmol) in MeOH (50 mL), THF (10 mL) was added MAGNESIUM (0.654 g, 26.9 mmol) which was pretreated with 1.0 N HCl and rinsed with MeOH, stirred at rt overnight. The Et2O was added and followed by Na2SO4.10H2O, stirred at room temperature for 1 hr, filtered, and filtrate was concentrated. The crude was purified by 40 g ISCO silica column, eluted with EA: HX-0-100%, the desired fractions were concentrated to yield 1-benzhydryl-4-(3-methyloxetan-3-yl)piperazine (1.08 g) as a white solid.

Workup

  1. washrinsed with MeOH
  2. additionThe Et2O was added
  3. stirringstirred at room temperature for 1 hr
  4. filtrationfiltered
  5. concentrationfiltrate was concentrated
  6. customThe crude was purified by 40 g ISCO silica column
  7. washeluted with EA
  8. concentrationHX-0-100%, the desired fractions were concentrated

Sources & evidence

ORD record
ord-d683b01101584b859730bec77e5c5d31
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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