Acetyl chloride → N-[4-Nitro-3-(piperidin-1-yl)phenyl]acetamide

HRID 32914Notes

Reaction equation

HRID 32914 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:26](=[O:28])[CH3:27])=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 541381144-Nitro-3-piperidin-1-yl-phenylamine

Product 1

HCID 53977390N-[4-Nitro-3-(piperidin-1-yl)phenyl]acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Nitro-3-piperidin-1-yl-phenylamine (64 mg, 0.28 mmol, as prepared in the previous step) and DIEA (122 μL, 0.700 mmol) in 4 mL of CH2Cl2 was treated with acetyl chloride (28 μL, 0.40 mmol). The reaction was stirred for 1 h, diluted with CH2Cl2 (25 mL), washed with water (50 mL), and dried (Na2SO4). Concentration of the solvent in vacuo afforded 51 mg (78%) of N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide. Using a procedure similar to Example 3, step (c), 4-nitro-3-piperidin-1-yl-phenylamine (51 mg, 0.21 mmol) was stirred with 5% Pd—C (35 mg) under H2 to afford 40 mg (61%) of the title compound as a dark semi-solid. Mass spectrum (ESI, m/z): Calcd. for C13H19N3O, 234.1 (M+H), found 234.2.

Workup

  1. washwashed with water (50 mL)
  2. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-00dfa48d797b4a3688e3562bf402a8db
Source dataset
uspto-grants-2008_09
Patent number
US07427683B2

Reaction notes

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