Triethylamine → HCID 21895260, compound

HRID 720778Notes

Reaction equation

HRID 720778 reaction equation
[C:1]([CH:3]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:4](Cl)=[O:5])#[N:2].Cl.[CH2:12]([C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[O:16][CH:17](N)[CH2:18][CH3:19])[CH3:13].C([N:27](CC)CC)C>C(Cl)Cl>[C:1]([CH:3]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:4]([NH:27][CH:18]([CH3:19])[CH2:17][O:16][C:15]1[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=1[CH2:12][CH3:13])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 125623142-Cyano-3,3-dimethylbutanoyl chlorideHCID 21895278HCID 21895278, compound

Product 1

HCID 21895260HCID 21895260, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-cyano-3,3-dimethylbutanoyl chloride (E. Schaumann, H. Mrotzek; J. Org. Chem., 1979, 35, 1965) (0.364 g, 2.28 mmol) in 10 mL methylene chloride was added dropwise to a solution of 1-(2-ethylphenoxy)propanamine hydrochloride (0.56 g, 2.6 mmol), triethyl amine (1.0 mL, 7.2 mol) in 30 mL methylene chloride. The reaction mixture was stirred for 2 h then concentrated in vacuo. The residue was purified by flash chromatography using 20% ethyl acetate/hexanes as eluent to give 0.290 g (42%) of the title compound as a white solid: mp 94–97° C., 1H NMR (CDCl3) δ 1.20 (m, 12H), 1.40 (m, 3H), 2.65 (q, 2H), 3.16 (dd, 1H), 3.98 (m, 1H), 4.05 (m, 1H), 4.40 (m, 1H), 6.00 (d, 1H), 6.25 (dd, 1H), 6.95 (t, 1H), 7.18 (t, 2H).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1718a38677b745c5aa8919eb351bb8e8
Source dataset
uspto-grants-2006_11
Patent number
US07135585B2

Reaction notes

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