Triethylamine → HCID 21895260, compound

HRID 478988Notes

Reaction equation

HRID 478988 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 mmol) 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) δ1.20 (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-0f6ee4a8d035426fbe5e0479dc40b3be
Source dataset
uspto-grants-2003_11
Patent number
US06642392B1

Reaction notes

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