Ethyl Acetate → HCID 19733830, compound

HRID 327803Notes

Reaction equation

HRID 327803 reaction equation
[CH3:1][NH:2][CH2:3][C:4]#[C:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CN(P(N(C)C)(N(C)C)=O)C.Br[CH2:24][CH:25]1[O:29][CH2:28][CH2:27][O:26]1.CCOC(C)=O>CN(C=O)C>[CH:25]1([CH2:24][N:2]([CH3:1])[CH2:3][C:4]#[C:5][CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[O:29][CH:28]=[CH:27][O:26]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12679HexamethylphosphoramideHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 5358932-Butyn-1-amine, N-methyl-4-(1-pyrrolidinyl)-

Product 1

HCID 19733830HCID 19733830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-Methyl-4-(1-pyrrolidinyl)-2-butynamine (83.4 mg, 0.548 mmol), TEA (153 μL, 1.098 mmol), HMPA (114 μL, 0.657 mmol), and 2-(bromomethyl)-1,3-dioxolane (68 μL, 0.657 mmol) in DMF (2 mL) was stirred at 50 ° C. for 20 h or until complete by TLC. The mixture was poured into EtOAc (20 mL) then washed with 1N NaOH saturated with NaCl (3×20 mL). The organic layer was dried over Na2SO4, and the EtOAc removed in vacuo to give a crude orange oil (102.8 mg, 79% yield). This oil was vacuum distilled to give N-(2,5-dioxolylmethyl)-N-methyl-4-(1-pyrrolidinyl)-2-butynamine as a clear oil: bp 90° C. (0.2 mm Hg); MS (CI-NH3), m/e 239 (MH+); 1H NMR (CDCl3) δ1.74 (br s, 4 H), 2.33 (s, 3 H), 2.58 (br H), 3.37 (s, 2 H), 3.38 (s, 2 H), 3.79 (m, 2 H), 3.92 (m, 2 H), 4.90 (t, J=4.6 Hz, 1 H).

Workup

  1. washthen washed with 1N NaOH saturated with NaCl (3×20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe EtOAc removed in vacuo
  4. customto give a crude orange oil (102.8 mg, 79% yield)
  5. distillationdistilled

Sources & evidence

ORD record
ord-82d329f7095a4f0e8b12ad268c98e32a
Source dataset
uspto-grants-1993_12
Patent number
US05274121

Reaction notes

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