Sodium Hydroxide → 3-[4-(4-Phenylamino-phenyl)-piperazin-1-yl]-propionic acid sodium salt

HRID 2353227Notes

Reaction equation

HRID 2353227 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[OH-].[Na+:27]>CO>[Na+:27].[C:19]1([NH:18][C:15]2[CH:14]=[CH:13][C:12]([N:9]3[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][C:3]([O-:25])=[O:2])[CH2:11][CH2:10]3)=[CH:17][CH:16]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 249362433-[4-(4-Phenylamino-phenyl)-piperazin-1-yl]-propionic acid methyl ester

Product 1

HCID 589025313-[4-(4-Phenylamino-phenyl)-piperazin-1-yl]-propionic acid sodium saltYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

The compound from Example 1 (85 mg, 0.25 mmol) was dissolved in methanol (2 mL) followed by addition of 1N NaOH aqueous solution (0.27 ml, 0.27 mmol). The reaction solution was stirred at 60-70° C. for 4 h and then evaporated under vacuum to dryness. The residue was stirred with ethyl acetate (2 mL) and the solid was collected by filtration and washed with ethyl acetate to give the title product as an off-white solid (78 mg, 89.9%): MS (ESI) m/z 325 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 1.99 (m, 2H), 2.45-2.51 (m, 6H), 3.01 (t, J=4.8 Hz, 4H), 6.67 (m, 1H), 6.88 (m, 4H), 6.98 (d, J=9.2 Hz, 2H), 7.13 (m, 2H), 7.75 (s, 1H).

Workup

  1. customevaporated under vacuum to dryness
  2. stirringThe residue was stirred with ethyl acetate (2 mL)
  3. filtrationthe solid was collected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-baa0d03301ba44dcbef6e2d20ac7f97b
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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