(R)-1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidine-3-carboxylic acid ethyl ester → (R)-1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidine-3-carboxylic acid hydrochloride

HRID 77071Notes

Reaction equation

C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:20]=3)[CH:13]=2)[CH2:7]1)=[O:5])C>Cl>[ClH:18].[NH:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[C:14]1[CH:13]=[C:12]([N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

Conditions

Temperature: 120 °C

Procedure

Method 2—Step e A mixture of (R)-1-[3-(1H-Benzoimidazol-2-yl)-4-chloro-phenyl]-piperidine-3-carboxylic acid ethyl ester (0.81 g, 2.11 mmol) in 6N HCl (4.0 mL) was heated in microwave at 120° C. for 20 minutes; 2 cycles were needed to complete conversion. Then solvent was removed and the crude triturated with a mixture of acetone/ethyl acetate (1:1), the solid filtered off and dried under vacuum, to obtain 0.60 g of the title compound (80%).

Workup

customThen solvent was removed
customthe crude triturated with a mixture of acetone/ethyl acetate (1:1)
filtrationthe solid filtered off
customdried under vacuum

Sources & evidence

ORD record: ord-9b4d3a1b858c4580a34adba456ac65d8
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835648B2

Reaction notes

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