HCID 9917300, compound → HCID 22318662, compound

HRID 497351Notes

Reaction equation

HRID 497351 reaction equation
[ClH:1].Cl.Cl.Cl.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.CCCCCC.C(O)(C)C.C(NCC)C>>[ClH:1].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)[CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 9917300HCID 9917300, compoundHCID 21973129Hexane isopropanol diethylamine

Product 1

HCID 22318662HCID 22318662, compound

Procedure

1-[2-(4-Fluorophenyl)-2-(4-methylpiperazino)ethyl]-4-[4-naphthalen-1-yl-butyl]piperazine hydrochloride obtained in Example 2 (6) was resolved by means of HPLC (Chiralpak AD (manufactured by Daicel Co.), 2φ×25 cm, mobile phase: hexane-isopropanol-diethylamine=95:5:0.1, flow rate 5.0 ml/min). After the resolution, the solvent was concentrated under reduced pressure, dissolved in ethanol, and introduced to the hydrochloride by 4M hydrogen chloride/ethyl acetate solution, and the solvent was concentrated under reduced pressure to give 1-[2-(4-fluorophenyl)-2-(4-methylpiperazino)ethyl]-4-[4-naphthalen-1-yl-butyl]piperazine hydrochloride (optically active compound).

Workup

  1. concentrationAfter the resolution, the solvent was concentrated under reduced pressure
  2. dissolutiondissolved in ethanol
  3. additionintroduced to the hydrochloride by 4M hydrogen chloride/ethyl acetate solution
  4. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2904b8b4a83749c9b14a77301bad5812
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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