Hydrochloric Acid → 3-Methylidene-2-oxo-1-azacyclotetradecane-14-carboxylic acid
Reaction equation
[O:1]=[C:2]1[CH:15]([C:16](O)=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:19]([OH:21])=[O:20])[NH:3]1.N1CCCCC1.C=O.Cl>N1C=CC=CC=1>[CH2:16]=[C:15]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:19]([OH:21])=[O:20])[NH:3][C:2]1=[O:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
2-oxo-1-azacyclotetradecane-3,14-dicarboxylic acid (0.868 g, 2.9 mmol) is dissolved in pyridine (15.0 mL). Piperidine (0.060 mL, 0.59 mmol) is added, followed by paraformaldehyde (0.133 g, 4.43 mmol), and the reaction is heated to 65° C. for 4 hours. The reaction is then cooled to 0° C., and concentrated hydrochloric acid is added to bring the pH to approximately 2. The reaction is partitioned between ethyl acetate and water, and the aqueous phase is extracted several times with ethyl acetate. The combined organic layers are dried (Na2SO4), and the solvent is evaporated to give 3-methylidene-2-oxo-1-azacyclotetradecane-14-carboxylic acid.
Workup
- temperatureThe reaction is then cooled to 0° C.
- customThe reaction is partitioned between ethyl acetate and water
- extractionthe aqueous phase is extracted several times with ethyl acetate
- dry with materialThe combined organic layers are dried (Na2SO4)
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-d4e78d67f9574f95b9763ece1f167e82
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05244889
Reaction notes
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