Nitrogen → HCID 87118843, compound

HRID 1622062Notes

Reaction equation

HRID 1622062 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[CH:7].C([O-])([O-])=[O:9].[K+].[K+].Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].N#N.C1[CH2:26][O:25][CH2:24][CH2:23]1>>[CH2:2]([N:1]([CH2:23][C:24]([O:25][CH3:26])=[O:9])[CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:3][CH2:4][CH2:5][C:6]#[CH:7]

Participants

6

Reactant 5

HCID 947NitrogenHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 10855384Hex-5-yn-1-amine

Product 1

HCID 87118843HCID 87118843, compoundYield 59%

Procedure

The 6-amino-hex-1-yne (0.3 g) was added to a stirring solution of 20 mL tetrahydrafuran (THF), 2 equiv. K2CO3, and 2.4 eq methyl bromoacetate. The mixture was further stirred at room temperature for 3 h under a stream of dry N2. The reaction was monitored by thin layer chromatography (TLC) using hexanes:ethyl acetate (=2:1) as the mobile phase, and the mixture was filtered after completion of the reaction. The filtrate was concentrated and purified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1). The final product, dimethyl 2,2′-(hex-5-ynylazanediyl)diacetate, was concentrated by rotary evaporation and acquired as a transparent oil. Yield was 59%. ESI-MS [M+H]+ m/z 242.1, 1H NMR (CDCl3) δ 3.71 (s, 6H), 3.56 (s, 4H), 2.73 (t, 2H), 2.22 (m, 2H), 1.94 (t, 1H), 1.57 (m, 4H).

Workup

  1. filtrationethyl acetate (=2:1) as the mobile phase, and the mixture was filtered
  2. customafter completion of the reaction
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography (silica gel, hexanes:ethyl acetate=1:1)
  5. concentrationThe final product, dimethyl 2,2′-(hex-5-ynylazanediyl)diacetate, was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-b0afeabbce54489e8ee23f7abcd6b0b1
Source dataset
uspto-grants-2014_07
Patent number
US08778626B2

Reaction notes

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