Sodium Iodide → HCID 10829224, compound

HRID 1602097Notes

Reaction equation

HRID 1602097 reaction equation
[CH3:1][O:2][CH:3]([O:9][CH3:10])[CH2:4][CH2:5][CH2:6][CH2:7]Br.C([O-])([O-])=O.[Na+].[Na+].[I-].[Na+].[N:19]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[Al]>C(COC)OC>[CH3:1][O:2][CH:3]([O:9][CH3:10])[CH2:4][CH2:5][CH2:6][CH2:7][N:22]1[CH2:21][CH2:20][N:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5359268AluminumHCID 110746845-bromo-1,1-dimethoxypentane

Product 1

HCID 10829224HCID 10829224, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-bromovaleraldehyde dimethyl acetal (27.5 g, 0.13 mol), Na2CO3 (20.7 g, 0.195 mol), sodium iodide (19.5 g, 0.13 mol) and tert-butyl 1-piperazinecarboxylate (25.5 g, 0.137 mol), in dimethoxyethane (250 ml), was heated at 100° C. for 3 h. Aluminium foil was wrapped around the vessel to exclude light. The mixture was cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure and then EtOAc (50 ml) added and the mixture filtered again to remove inorganic salts. The solvent was removed under vacuum and the residue chromatographed on silica gel eluting with EtOAc to give the title-product (25.7 g, 63%). δ(250 MHz, CDCl3) 1.29-1.71 (6H, m, 3 of CH2); 1.46 (9H, s, OC(Me)3); 2.31-2.39 (6H, m, 3 of CH2); 3.32 (6H, s, CH(OMe)2); 3.41-3.45 (4H, m, 2 of CH2); 4.36 (1H, t, J=6 Hz, CH(OMe)2).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under reduced pressure
  3. additionEtOAc (50 ml) added
  4. filtrationthe mixture filtered again
  5. customto remove inorganic salts
  6. customThe solvent was removed under vacuum
  7. customthe residue chromatographed on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-1a21739e06594d10923f77136a855a64
Source dataset
uspto-grants-1999_11
Patent number
US05981529

Reaction notes

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