1-(3,4-Dichlorophenyl)piperazine → HCID 69517535, compound

HRID 1831257Notes

Reaction equation

HRID 1831257 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[CH:7][CH:6]=1)=[O:3].[Cl:22][C:23]1[CH:24]=[C:25]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:26]=[CH:27][C:28]=1[Cl:29]>>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([O:4][C:2]([N:33]3[CH2:32][CH2:31][N:30]([C:25]4[CH:26]=[CH:27][C:28]([Cl:29])=[C:23]([Cl:22])[CH:24]=4)[CH2:35][CH2:34]3)=[O:3])=[CH:6][CH:7]=2)=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 936011-(3,4-Dichlorophenyl)piperazineHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformate

Product 1

HCID 69517535HCID 69517535, compound

Procedure

The hydrochloride of the title compound was prepared from 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate and 1-(3,4-dichlorophenyl)piperazine. The crude product was partitioned between dichlorormethane and 2 M aqueous sodium carbonate. The organic layer was washed with water, dried and evaporated. The residue was triturated with ethyl acetate-heptane (1:4) and the precipitate was collected by filtration and dried to give the title compound as white crystals. Yield 28%; m.p. 115–116° C.; 1H NMR (DMSO-d6): δ 8.61–8.55 (br, 1H), 8.30–8.20 (dd-like, 1H), 7.48–7.40 (d-like,1H), 7.31–7.16 (m, 6H), 7.04–6.94 (dd-like, 1H), 3.83–3.47 (br m, 4H), 3.36–3.24 (br s, 4H+water); HPLC-MS: m/z=512 (M+H); IR (KBr): ν 1724, 1706 cm−1.

Workup

  1. customThe crude product was partitioned between dichlorormethane and 2 M aqueous sodium carbonate
  2. washThe organic layer was washed with water
  3. customdried
  4. customevaporated
  5. customThe residue was triturated with ethyl acetate-heptane (1:4)
  6. filtrationthe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-429b7067bf0443efba02d0ddff7a5a31
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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