Acetic Acid → HCID 66711883, compound

HRID 1262077Notes

Reaction equation

HRID 1262077 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[C:25]([O:32][CH3:33])[CH:24]=3)[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>[Zn].C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[C:25]([O:32][CH3:33])[CH:24]=3)[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66711294HCID 66711294, compound

Product 1

HCID 66711883HCID 66711883, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[1-(3-Methoxy-4-nitro-phenyl)-piperidin-4-yl]-piperazine-1-carboxylic acid benzyl ester (0.20 g, 0.44 mmol), Acetic acid (2 mL, 30 mmol), Ethanol (2 mL) and Zinc (0.20 g, 3.0 mmol) was stirred at room temperature for 3 hours. The reaction was filtered and evaporated. To the residue was added a saturated sodium bicarbonate solution and DCM, separated, dried and evaporated to give 4-[1-(4-Amino-3-methoxy-phenyl)-piperidin-4-yl]-piperazine-1-carboxylic acid benzyl ester as a dark blue solid (0.155 g, 82%). LCMS (m/e) 424 (M); 1H-NMR (DMSO-d6, 400 MHz) δ7.387.36 (m, 5H), 6.48 (s, 2H), 6.13 (s, 1H), 5.07 (s, 2H), 4.20 (br, 2H), 3.73 (s, 3H), 3.39 (m, 6H), 1.80 (m, 2H, 0.80 (m, 2H).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated
  3. additionTo the residue was added a saturated sodium bicarbonate solution and DCM
  4. customseparated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-b83b88366f914e97a06441652109122c
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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