Water → HCID 53926811, compound

HRID 1389996Notes

Reaction equation

HRID 1389996 reaction equation
[H-].[Na+].[OH:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.I[CH3:18].O>CN(C=O)C>[CH3:18][O:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2029451877278-41-2

Product 1

HCID 53926811HCID 53926811, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 57% oil dispersion containing 0.6 g (0.025 mole) NaH was added in one portion to a solution of 4.7 g (0.023 mole) 1-hydroxy-4-(1,1-dimethylethoxycarbonyl)piperazine in 100 ml DMF under a dry N2 atmosphere. The mixture was stirred for 2 hours at room temperature and then 6.5 g (0.046 mole) iodomethane was added over 1 minute. After stirring for an additional 15 minutes, the mixture was poured into 100 ml H2O, stirred briefly, and extracted thoroughly with low boiling (35°-65° C.) petroleum ether. The extracts were dried (MgSO4), filtered and evaporated in vacuo to give 1.8 g of an oil. The oil was dissolved in ethyl ether, washed with dilute aqueous HCl, dried (MgSO4), filtered, and evaporated in vacuo to yield 1.3 g yellow oil. Short path distillation (Kugelrohr) returned 0.8 g colorless distillate, b.p.* 55°-65° C./0.15 mm. Calc. for C10H 20 N2O3 (216.28): C, 55.53; H, 9.32; N, 12.95; O, 22.19. Found: C, 55.61; H, 9.13; N, 12.96; O, 22.33.

Workup

  1. stirringAfter stirring for an additional 15 minutes
  2. stirringstirred briefly
  3. extractionextracted thoroughly with low boiling (35°-65° C.) petroleum ether
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5dcaa713959d4c8b891bd884f74926e9
Source dataset
uspto-grants-1981_01
Patent number
US04247549

Reaction notes

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