Acetic Anhydride → 1-Acetyl-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

HRID 419372Notes

Reaction equation

HRID 419372 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH3:24][C:25](OC(C)=O)=[O:26]>C(Cl)Cl>[C:25]([N:21]1[CH2:20][CH2:19][N:18]([CH:15]2[CH2:14][CH2:13][N:12]([C:5]3[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:17][CH2:16]2)[CH2:23][CH2:22]1)(=[O:26])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 598602641-{1-[3-(Methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Product 1

HCID 574161491-Acetyl-4-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (Example 57, step C) (0.500 g, 1.56 mmol) in DCM (20 mL) was added Ac2O (0.22 mL, 2.34 mmol). TEA (0.33 mL, 2.34 mmol) was then added dropwise and the resultant mixture was stirred at rt overnight. TLC indicated that the reaction had gone to completion. The reaction mixture was evaporated onto silica gel and purified by flash chromatography to afford the title compound of step A (0.52 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 7.85 (d, J=9.6 Hz, 1H), 6.57 (dd, J=9.5, 2.5 Hz, 1H), 6.48 (d, J=2.6 Hz, 1H), 4.07-4.00 (m, 2H), 3.88 (s, 3H), 3.41-3.34 (m, 4H), 2.99-2.89 (m, 2H), 2.43-2.36 (m, 2H), 1.95 (s, 3H), 1.85-1.78 (m, 2H), 1.48-1.38 (m, 2H).

Workup

  1. customThe reaction mixture was evaporated onto silica gel
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-22405836d06b4542bebdb4398d5f33c1
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…