Hydrochloric Acid → [3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid

HRID 1486721Notes

Reaction equation

HRID 1486721 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+].Cl>C1COCC1.CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([NH:19][C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[CH2:12][N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[O:28])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 867065481-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 86706549[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acidYield 91.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[3-(4-chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester (1.65 g, 4.12 mmol) in a mixture of THF (20 mL) water (10 mL) and MeOH (10 mL) is treated with lithium hydroxide monohydrate (190 mg, 4.53 mmol) at RT for 2 h. Aq. 2N HCl (2.3 mL) is added and the resulting solution is lyophilized to yield the crude title compound (1.41 g) containing one equivalent LiCl. LC-MS A: tR=0.64 min; [M+H]+=372.93.

Sources & evidence

ORD record
ord-855053f2e32d4576958124f46c484557
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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