Methanol → METHYL 3-(4-METHOXYBENZYLAMINO)PROPANOATE

HRID 1808017Notes

Reaction equation

HRID 1808017 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH3:11][OH:12]>>[CH3:11][O:12][C:3](=[O:2])[CH2:4][CH2:5][NH:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 887Methanol2×HCID 754524-Methoxybenzylamine

Product 1

HCID 12201326METHYL 3-(4-METHOXYBENZYLAMINO)PROPANOATE

Procedure

A solution of p-methoxybenzyl amine (690 mg, 722 μL, 8.01 mmol) in dry methanol (5 ml), under nitrogen was cooled to 0° and treated dropwise with a solution of metacrylate (951 μL, 1.0 g, 7.28 mmol) in MeOH (1.0 ml) added over 2 min. After 15.5 h the clear solution was distilled at atmospheric pressure to remove MeOH. The high boiling residue (>170) formed 3-(4-Methoxy-benzylamino)-propionic acid methyl ester (1.88 g, Quantitative) 1H (300 MHz, CDCl3) 1.78 (bs, 1H), 2.45 and 2.53 (t, J=3.0 Hz, 2H), 2.77 and 2.87 (t, J=3.0 Hz, 2H), 3.46 and 3.67 (s, 3H), 3.64 and 3.73 (s, 3H), 3.88 (m, 2H), 6.78 and 6.85 (m, 2H), 7.17 and 7.23 (m, 2H).

Workup

  1. additionadded over 2 min
  2. distillationAfter 15.5 h the clear solution was distilled at atmospheric pressure
  3. customto remove MeOH

Sources & evidence

ORD record
ord-a56bd46995544633b9c804c6176aa004
Source dataset
uspto-grants-2013_01
Patent number
US08357718B2

Reaction notes

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