Lithium Hydroxide → HCID 68487904, compound

HRID 1046331Notes

Reaction equation

HRID 1046331 reaction equation
[CH3:1][N:2]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.[OH-].[Li+].C(O)(C(F)(F)F)=O>C1COCC1>[CH3:1][N:2]([CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][CH:27]=1)[CH:3]1[CH2:4][CH2:5][N:6]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 68489594HCID 68489594, compound

Product 1

HCID 68487904HCID 68487904, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[[4-[methyl[2-(4-phenoxyphenyl)ethyl]amino]-1-piperidinyl]methyl]benzoate (about 0.71 mmol) in aqueous THF was treated with an aqueous solution of lithium hydroxide. The reaction was acidified with TFA. Purification by preparatory HPLC gave 40 mg of 4-[[4-[methyl[2-(4-phenoxyphenyl)ethyl]amino]-1-piperidinyl]methyl]benzoic acid; 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, 2H), 7.56 (dbr, 2H), 7.32 (ddd, 2H), 7.26 (d, 2H), 7.07 (tt, 1H), 6.88-6.96 (m, 4H), 4.27 (br, 2H), 3.25 (br, 3H), 2.86 (br, 4H), 2.72 (s, 3H), 2.14 (br, 2H) 1.85 (br, 2H) ppm.

Workup

  1. customPurification by preparatory HPLC

Sources & evidence

ORD record
ord-37128a86fb1744268ac61f511a807074
Source dataset
uspto-grants-2013_10
Patent number
US08569303B2

Reaction notes

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