Sodium hydride → HCID 59135577, compound

HRID 1972721Notes

Reaction equation

HRID 1972721 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15]Cl)[CH:10]([CH2:18][OH:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[CH:10]([CH2:18][O:19][CH2:15][C:14]2=[O:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58529757HCID 58529757, compound

Product 1

HCID 59135577HCID 59135577, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 1-(4-Benzyl-2-hydroxymethyl-piperazin-1-yl)-2-chloro-ethanone (425 mg, 1.50 mmol) in anhydrous THF (10 mL) under N2 was added 60% sodium hydride (240.5 mg, 6.0 mmol, 4.0 eq). The mixture was stirred at rtT for 6 h and quenched with aqueous, saturated NH4Cl solution. The mixture was poured into EtOAc, and the organic layer was washed with 50% aqueous brine (3×), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC (Biotage®, gradient elution 75 to 100% EtOAc/hexane) to give the product (265 mg, 72%) as clear oil. 1H-NMR (300 MHz, DMSO-d6) 7.34 to 7.24 (m, 5H), 4.34 to 4.29 (m, 1H), 3.99 (s, 2H), 2.92 (dd, 1H), 3.57 to 3.52 (m, 1H), 3.49 (d, 2H), 3.47 to 3.42 (dd, 1H), 2.82 to 2.74 (m, 2H), 2.69 (dt, 1H), 1.89 (dt, 1H), 1.77 (t, 1H); ES-MS m/z 247.2 [M+H]+, RT (min) 1.07.

Workup

  1. customquenched with aqueous, saturated NH4Cl solution
  2. additionThe mixture was poured into EtOAc
  3. washthe organic layer was washed with 50% aqueous brine (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by MPLC (Biotage®, gradient elution 75 to 100% EtOAc/hexane)

Sources & evidence

ORD record
ord-f1cf3184e5c74d1ab5f2c845c0935515
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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