Hydrochloric Acid → Ethyl 4-hydroxypiperidine-4-carboxylate

HRID 712250Notes

Reaction equation

[OH:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.[CH3:12][CH2:13]O>>[OH:1][C:2]1([C:8]([O:10][CH2:12][CH3:13])=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 44371984-hydroxypiperidine-4-carboxylic Acid

Product 1

HCID 22717992Ethyl 4-hydroxypiperidine-4-carboxylate

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-hydroxypiperidine-4-carboxylic acid (1.20 g, 8.26 mmol) in EtOH (30 ml) was added conc. HCl (5 ml) at rt and the mixture heated up to 80° C. for 2-3 h. After completion (by TLC), solvent was evaporated under reduced pressure to obtain the desired product (1.20 g, crude) which was carried forward for next step without further purification. 1H NMR (D2O): δ 4.20 (q, J=7.20 Hz, 2H), 3.28 (M, 4H), 2.22 (m, 2H), 1.91 (m, 2H), and 1.22 (t, J=7.20 Hz, 3H).

Workup

customAfter completion (by TLC), solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-be55e4bfe4414e40959400e0b8e12611
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181234B2

Reaction notes

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