N-Methylbutylamine → HCID 60134574, compound

HRID 2061084Notes

Reaction equation

HRID 2061084 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH3:6].[N:7]([C:10]([CH3:16])([CH3:15])[CH2:11][C:12](Cl)=[O:13])=[N+:8]=[N-:9]>ClCCCl>[N:7]([C:10]([CH3:16])([CH3:15])[CH2:11][C:12]([N:2]([CH2:3][CH2:4][CH2:5][CH3:6])[CH3:1])=[O:13])=[N+:8]=[N-:9]

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 601345073-Azido-3-methylbutanoyl chloride

Product 1

HCID 60134574HCID 60134574, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred ice cold solution of N-methylbutan-1-amine (8.88 mL, 2 equiv, 74.4 mmol) in anhydrous DCE (65 mL) was added 3-azido-3-methylbutanoyl chloride (6.02 g, 37.2 mmol) in small portions over 5 min. The reaction was removed from the ice bath and stirred at room temperature for 1 h. The reaction mixture was poured into a separatory funnel and washed with 1 M HCl (2×100 mL). The organic layer was separate and dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a yellow oil (7.11 g, 90.1%). This material was used without further purification. 1HNMR (CDCl3, 400 MHz): δ 0.91-0.98 (m, 3H), 1.27-1.37 (m, 2H), 1.46 (s, 6H), 1.47-1.57 (m, 2H), 2.49 (s, 2H), 2.92 (s, 1.35H), 3.02 (s, 1.48H) methyl rotamers, 3.28-3.39 (m, 2H). LRMS (ESI+) for C10H20N4O (212.2); Found: 213 (MH+).

Workup

  1. customThe reaction was removed from the ice bath
  2. additionThe reaction mixture was poured into a separatory funnel
  3. washwashed with 1 M HCl (2×100 mL)
  4. customThe organic layer was separate
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-232bb574df024160b52e9fcc08b87103
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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