Acetic Anhydride → 1-[4-(4-Phenoxy-phenyl)-piperazin-1-yl]-ethanone

HRID 2353258Notes

Reaction equation

HRID 2353258 reaction equation
Cl.[O:2]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].C(N(CC)CC)C>C(Cl)Cl>[O:2]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 448188041-(4-Phenoxyphenyl)piperazine hydrochloride

Product 1

HCID 236277341-[4-(4-Phenoxy-phenyl)-piperazin-1-yl]-ethanoneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound from Example 8, step 2 (100 mg 0.3 mmol) in CH2Cl2 was added acetic anhydride (0.1 mL) and triethylamine (0.4 mL) sequentially at rt. The reaction mixture was stirred at it for 1 h and poured onto water (100 mL). The precipitate was collected by filtration and washed with water to give the title compound (58 mg, 64%) as an off-white solid: MS (ESI) m/z 297 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.15 (s, 3H), 3.12 (m, 4H), 3.63 (t, J=5.2 Hz, 2H), 3.78 (t, J=5.2 Hz, 2H), 6.91-6.99 (m, 6H), 7.05 (m, 1H), 7.28-7.32 (m, 2H).

Workup

  1. additionpoured onto water (100 mL)
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-44a78e61653b46269af4be5d79e8e58a
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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