Hydrochloric Acid → [4-(4-But-2-ynyloxy-benzoyl)-piperidin-1-yl]-acetic acid

HRID 713466Notes

Reaction equation

F[C:2]1[CH:19]=[CH:18][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH2:20]([OH:24])[C:21]#[C:22][CH3:23].[OH-].[Na+].Cl>O>[CH2:20]([O:24][C:2]1[CH:19]=[CH:18][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1)[C:21]#[C:22][CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of [4-(4-fluoro-benzoyl)-piperidin-1-yl]-acetic acid (561 mg, 2.11 mmol) in water (10 mL) and was added 2-butyn-1-ol (3.71 g, 52.9 mmol) followed by a solution of 4N NaOH (3.44 mL, 13.8 mmol). The reaction was heated up to 80° C. for 72 hours. The reaction was acidified using 2N HCl to pH 5, then the solvent was then removed under vacuum to afford the crude title compound (2.0 g). LRMS m/z: ES+=315.9 (M+H), retention time 1.52.

Workup

customthe solvent was then removed under vacuum

Sources & evidence

ORD record: ord-24f503af8ee74185a9c80049bd602d08
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181266B2

Reaction notes

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