Hydrochloric Acid → Methyl 6-aminohexanoate
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].Cl.[CH3:11]O>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:11])=[O:8]Participants
4
Procedure
To a suspension of 6-aminocaproic acid (3.00 g, 22.9 mmol) in anhydrous MeOH (60 mL), was introduced hydrogen chloride gas for 25 min., during which time the suspension became clear. The solution was then stirred at room temperature for 5 hours. MeOH was removed in vacuo. The residue was recrystallized from THF to give a white solid (1) (3.10 g). (Yield: 75%). The compound is better stored in hydrochloride form, because its free amino form tends to polymerize. 1HNMR (MeOH-d4, 300 MHz) δ 3.66 (s, 3H, OCH3), 2.92 (t, 2H, J=7.7 Hz, NCH2), 2.37 (t, 2H, J=7.2 Hz, CH2CO2), 1.74-1.60 (m, 4H, CH2CH2), 1.48-1.36 (m, 2H, CH2).
Workup
- customMeOH was removed in vacuo
- customThe residue was recrystallized from THF
Sources & evidence
- ORD record
- ord-a2b6458b2c634bc2936610eb6eea6e19
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06107489
Reaction notes
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