Hydrochloric Acid → 3-(4-(Tert-butoxycarbonyl)piperazin-1-yl)benzoic acid

HRID 1803870Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 1-Boc-4-[3-(ethoxycarbonyl)phenyl]piperazine (200 mg, 0.6 mmol) in EtOH (1 ml), 2M NaOH (1 ml, 2 mmol) was added. The reaction was heated for 2 hours at 40° C. until HPLC revealed the disappearance of the starting material. The solution was neutralized to pH 7 with aqueous 25% HCl. The precipitate was filtrated and washed with Et2O to afford the desired final compound as beige solid (80 mg, 40%).

Workup

filtrationThe precipitate was filtrated
washwashed with Et2O

Sources & evidence

ORD record: ord-184d586ede4e475bb7f7eb8f7305183a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354399B2

Reaction notes

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