1-(2-Methoxyphenyl)-4-(1-(4-phenylphenyl)cyclohex-1-en-4-yl)piperazine → HCID 178489564, compound

HRID 54202Notes

Reaction equation

HRID 54202 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH:15]2[CH2:20][CH2:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:23][CH:22]=3)=[CH:17][CH2:16]2)[CH2:11][CH2:10]1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][CH:26]=3)[CH2:17][CH2:16]2)[CH2:13][CH2:14]1

Participants

4

Reactant 1

HCID 199585511-(2-Methoxyphenyl)-4-(1-(4-phenylphenyl)cyclohex-1-en-4-yl)piperazine

Product 1

HCID 178489564HCID 178489564, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1-(2-Methoxyphenyl)-4-(1-(4-phenylphenyl)cyclohex-1-en-4-yl)piperazine (2.7 g, 5.4 mmol) was hydrogenated at 50 psi (about 3.5×105N.m-2) above atmospheric pressure at 45° C. in acetic acid (50 ml), using 10% Pd/C (2.4 g) as a catalyst for three days. The volatiles were evaporated in vacuo and the residue was partitioned between dichloromethane (150 ml) and sat. NaHCO3 (200 ml). The organic layer was separated and washed with brine and evaporated in vacuo. The residues were recrystallised from dichloromethane and again from methanol. The white solid was dissolved in ether and acidified to pH 1 with ethereal HCl. The volatiles were removed in vacuo to give the title compound as the one and a half hydrochloride; three quarters hydrate (0.281 g), m.p. 220°-225° C.

Workup

  1. customfor three days
  2. customThe volatiles were evaporated in vacuo
  3. customthe residue was partitioned between dichloromethane (150 ml) and sat. NaHCO3 (200 ml)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customevaporated in vacuo
  7. customThe residues were recrystallised from dichloromethane and again from methanol
  8. dissolutionThe white solid was dissolved in ether
  9. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-d55d7cc28e1a48f58fe03a4724d0e591
Source dataset
uspto-grants-1997_04
Patent number
US05622951

Reaction notes

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