Lithium Hydroxide → HCID 58425657, compound

HRID 1966481Notes

Reaction equation

HRID 1966481 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:13]=2)[CH2:7]1)=[O:5])C.[OH-].[Li+]>C1COCC1.O>[CH2:22]([NH:21][C:14]1[CH:13]=[C:12]([N:8]2[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:17]=[CH:16][C:15]=1[N+:18]([O-:20])=[O:19])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67389707HCID 67389707, compound

Product 1

HCID 58425657HCID 58425657, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To stirred solution of ethyl-1-(3-(benzylamino)-4-nitrophenyl)piperidine-3-carboxylate (1 g, 3.1 mmol) in 10 ml THF: H2O (3:1) was added lithium hydroxide (0.35 g, 15.4 mmol) at room temperature. The resulting mixture was stirred for 5 h, solvent was evaporated and residue was dissolved in water washed with dichloromethane. The aqueous layer was then neutralised with 2M HCl to get yellow solid 1-(3-(benzylamino)-4-nitrophenyl)piperidine-3-carboxylic acid (0.7 g), 86% yield: 1H NMR (500 MHz, DMSO): δ 1.55 (m, 1H), 1.87 (m, 2H), 2.10 (m, 1H), 2.62 (m, 1H), 3.07 (m, 1H), 3.30 (m, 1H), 3.60 (m, 1H), 3.82 (dd, J=3.6, 5.6 Hz, 1H), 4.55 (d, J=5.4 Hz, 2H), 5.92 (d, J=2.5 Hz, 1H), 6.28 (dd, J=2.6 Hz, 1H), 7.32 (m, 2H), 7.41 (m, 3H), 8.12 (d, J=9.6 Hz, 1H), 8.8 (m, 1H).

Workup

  1. customsolvent was evaporated
  2. dissolutionresidue was dissolved in water
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-4f0c8c3ccf634ce3bfc2ac27149c49cc
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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