Water → HCID 21478844, compound

HRID 2292574Notes

Reaction equation

HRID 2292574 reaction equation
Cl[CH2:2][C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.O>ClCCl>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([CH2:2][C:3](=[O:11])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 2363491-Chloro-3-phenylpropan-2-one

Product 1

HCID 21478844HCID 21478844, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-chloro-3-phenyl-propan-2-one (10 g, 59 mmol) in dichloromethane (100 ml) was added benzylpiperazine (12.3 ml, 71 mmol) and triethylamine (8.2 ml, 59 mmol). The yellow solution was stirred overnight at ambient temperature and water was added (50 ml). The organic phase was decanted, washed with brine (50 ml), dried (sodium sulphate) and evaporated. The residue was purified by column chromatography on silica using petroleum ether (60-80) ethyl acetate to afford a yellow oil (2.4 g, 13%). 1H NMR (250 MHz, CDCl3) δ 2.30-2.64 (8H, m), 3.19 (2H, s), 3.51 (2H, s), 3.74 (2H, s), 7.17-7.38 (10H, m).

Workup

  1. customThe organic phase was decanted
  2. washwashed with brine (50 ml)
  3. dry with materialdried (sodium sulphate)
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-908c5635be3f4d0d9f6d3d4866f7da49
Source dataset
uspto-grants-1997_11
Patent number
US05684006

Reaction notes

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