Diisopropylethylamine → HCID 86642706, compound

HRID 2061100Notes

Reaction equation

HRID 2061100 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CCN(C(C)C)C(C)C.[N:24]([C:27]([CH3:33])([CH3:32])[CH2:28][C:29](Cl)=[O:30])=[N+:25]=[N-:26]>C(Cl)Cl>[N:24]([C:27]([CH3:33])([CH3:32])[CH2:28][C:29]([N:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:1])=[O:30])=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81746N-Methyl-1-dodecanamineHCID 601345073-Azido-3-methylbutanoyl chloride

Product 1

HCID 86642706HCID 86642706, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred ice cold solution of N-methyldodecanamine (5.0 g, 25.1 mmol) and DIEA (5.70 mL, 1.3 equiv, 32.6 mmol) in anhydrous DCM (150 mL) was added 3-azido-3-methylbutanoyl chloride (4.05 g, 1 equiv, 25.1 mmol) in small portions. The ice bath was removed and the reaction was stirred and left at room temperature for 3 h. The content of the reaction was poured into a separatory funnel. The organic layer was washed with 1 M HCl (3×100 mL) and saturated NaHCO3 (2×100 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (8.08 g, quant). This material was purified on an ISCO flash chromatography system with a gradient from 10-40% ethyl acetate and hexanes as eluent. The desired fractions were collected and concentrated to give a pale yellow oil (7.28 g, 89.3%). 1H NMR (CDCl3, 400 MHz): δ 0.88-0.94 (m, 3H), 1.26-1.35 (m, 6H), 1.47-1.48 (d, J=4, 6H), 1.50-1.59 (m, 2H), 2.51 (s, 2H), 2.94-3.04 (d, J=40, 3H), 3.30-3.40 (m, 2H). LRMS (ESI+) for C18H36N4O (324.3); Found: 325 (MH+).

Workup

  1. customThe ice bath was removed
  2. additionThe content of the reaction was poured into a separatory funnel
  3. washThe organic layer was washed with 1 M HCl (3×100 mL) and saturated NaHCO3 (2×100 mL)
  4. dry with materialIt was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under high vacuum
  8. customto give a crude oil (8.08 g, quant)
  9. customThis material was purified on an ISCO flash chromatography system with a gradient from 10-40% ethyl acetate and hexanes as eluent
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2280c806362343af8e44fddeb82f7bc6
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

Loading…