Allylamine → HCID 19380940, compound

HRID 1198491Notes

Reaction equation

HRID 1198491 reaction equation
[CH2:1](N)[CH:2]=C.C[N:6]1[CH2:11][CH2:10][O:9]CC1.[Cl:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=O>C(#N)C>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][C:10]([CH:11]([NH2:6])[CH:1]=[CH2:2])=[O:9]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 79724-MethylmorpholineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 19380940HCID 19380940, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of allyl amine 25 (2.0 g, 27 mmol), NMM (8.9 mL, 81 mmol), and acetonitrile (140 mL), at ambient temperature was added 4-chlorobutyryl chloride (3.4 mL, 27 mmol). After 20 hours the reaction mixture was concentrated. The residue was dissolved in ethyl acetate and then washed with water, 5% KHSO4 and brine, dried (MgSO4), and concentrated to give 26 (4.1 g, 87%) as a yellow oil. TLC Rf=0.17 (40% ethyl acetate/hexanes).

Workup

  1. concentrationAfter 20 hours the reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, 5% KHSO4 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00182906713e4ba78a56709ea6e2c565
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

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