Ethanol → 2-(1-Tert-butoxycarbonylpiperidin-4-yloxy)-4-(dimethyl-amino)benzoic acid

HRID 644159Notes

Reaction equation

[OH-].[K+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[CH:26]=[C:25]([N:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(O)C>O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[CH:26]=[C:25]([N:27]([CH3:29])[CH3:28])[CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium hydroxide (3.79 g, 67.5 mmol) in water (135 mL) was added to a mixture of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(N,N-dimethylamino)-benzoate (5.11 g, 13.5 mmol) and ethanol. The reaction was heated to 70° C. for 14 hours. The ethanol was removed in vacuo. The resulting aqueous mixture was cooled to 5° C., acidified with satd citric acid, filtered with water wash, and vacuum dried to give the desired product as a white solid (4.65 g, 95%).

Workup

customThe ethanol was removed in vacuo
temperatureThe resulting aqueous mixture was cooled to 5° C.
filtrationfiltered with water
washwash
customvacuum dried

Sources & evidence

ORD record: ord-209cad99f2ba48e49c5dc6eab4a2c67c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700628B2

Reaction notes

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