Lithium Hydroxide → HCID 67183654, compound

HRID 1966478Notes

Reaction equation

HRID 1966478 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([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)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Li+]>C1COCC1.O>[CH2:22]([NH:21][C:14]1[CH:13]=[C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]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 46199378HCID 46199378, compound

Product 1

HCID 67183654HCID 67183654, compoundYield 90%

Reagents, catalysts & solvents 1

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

Procedure

To stirred solution of ethyl-1-(3-(benzylamino)-4-nitrophenyl)piperidine-4-carboxylate (2 g, 6.2 mmol) in 20 ml THF: H2O (3:1) was added lithium hydroxide (0.740 g, 30.9 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-4-carboxylic acid (1.5 g), 90% yield: 1H NMR (500 MHz, DMSO): δ 1.46 (m, 2H), 1.80 (m, 2H), 3.03 (m, 2H), 3.82 (m, 2H), 4.59 (d, J=5.7 Hz, 2H), 5.94 (d, J=2.5 Hz, 1H), 6.40 (dd, J=2.5 Hz, 1H), 7.27 (m, 1H), 7.37 (m, 2H) 7.42 (m, 2H), 7.90 (d, J=9.8 Hz, 1H), 8.83 (m, 1H). HRMS (ESI) calculated for C19H21N3NaO4: 378.1424, Found: 378.1417.

Workup

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

Sources & evidence

ORD record
ord-74d87b5238de4542a2c6c3754a318390
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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