HCID 22122072, compound → HCID 178505744, compound

HRID 1858946Notes

Reaction equation

HRID 1858946 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:20][CH2:19]3)[CH2:14][CH:13]=2)=[CH:4][CH:3]=1>C(O)(=O)C.[Pt]=O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]2[CH2:13][CH2:14][C@H:15]([N:18]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:22][CH2:23]3)[CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 22122072HCID 22122072, compound

Product 1

HCID 178505744HCID 178505744, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of platinum oxide (0.1 g) and 1-[4-(4-fluoro-1-naphthalenyl)-3-cyclohexen-1-yl]-4-(phenylmethyl)piperazine (1.1 g, 2.7 mmole) was hydrogenated for 13 hr in 20 ml acetic acid. The catalyst was removed and the solution concentrated in vacuo. The residue was suspended in water and the mixture basified with potassium carbonate. The mixture was extracted with ether, the extracts were dried over sodium sulfate and the solution concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 2-propanol-ethyl acetate-hexane (3:10:87). Fractions containing the less polar material were concentrated in vacuo to give the cis isomer (25%, mp: 130-132° C.). Calc'd for C27H31FN2.0.1H2O: C, 80.21%; H, 7.78%; N, 6.93%. Found: C, 80.12%; H, 7.80%; N, 6.89%.

Workup

  1. customThe catalyst was removed
  2. concentrationthe solution concentrated in vacuo
  3. extractionThe mixture was extracted with ether
  4. dry with materialthe extracts were dried over sodium sulfate
  5. concentrationthe solution concentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel eluting with 2-propanol-ethyl acetate-hexane (3:10:87)
  7. additionFractions containing the less polar material
  8. concentrationwere concentrated in vacuo
  9. customto give the cis isomer (25%, mp: 130-132° C.)

Sources & evidence

ORD record
ord-bf6e6a0d86494279b38b6b405efc3bc9
Source dataset
uspto-grants-2000_11
Patent number
US06153611

Reaction notes

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