Hydrochloric Acid → Methyl 6-imino-6-methoxyhexanoate

HRID 870572Notes

Reaction equation

HRID 870572 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[N:10].[CH2:12]([O:14]CC)C>CO>[NH:10]=[C:9]([O:14][CH3:12])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH3:2])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 554130Methyl 5-cyanopentanoate

Product 1

HCID 23189824Methyl 6-imino-6-methoxyhexanoateYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bubble hydrogen chloride (g) through a 0° C. solution of 5-cyano-pentanoic acid methyl ester (3.0 mL; 1.00 equiv; 22.02 mmoles) in methanol (5 mL), and ethyl ether (10 mL) for 1 hour. Allow the solution to warm to room temperature then add 50 mL ethyl ether, stir vigorously for 15 minutes, then filter and collect the resulting precipitate. Wash the solid with ethyl ether to afford methyl 6-imino-6-methoxy-hexanoate (3.82 g; 83%): 1H NMR (DMSO) δ 1.47-1.62 (m, 4H), 2.31 (t, 2H), 2.59 (t, 2H), 3.56 (s, 3H), 4.03 (s, 3H).

Workup

  1. filtrationfilter
  2. customcollect the resulting precipitate
  3. washWash the solid with ethyl ether

Sources & evidence

ORD record
ord-c98fa7a79c2c40388b3ab71576959e67
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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