Potassium Carbonate → Cyclopropyl-[4-(6-methoxy-indan-1-yl)-piperazin-1-yl]-methanone

HRID 1956152Notes

Reaction equation

HRID 1956152 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>>[CH:18]1([C:21]([N:15]2[CH2:14][CH2:13][N:12]([CH:9]3[C:10]4[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=4)[CH2:7][CH2:8]3)[CH2:17][CH2:16]2)=[O:22])[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 22038119(6-Methoxy-indan-1-yl)piperazine

Product 1

HCID 22375366Cyclopropyl-[4-(6-methoxy-indan-1-yl)-piperazin-1-yl]-methanoneYield 75%

Procedure

A mixture of (6-methoxy-indan-1-yl)piperazine (3.0 g, 15.5 mmol), cyclopropane-carbonyl chloride (1.6 g, 15.5 mmol), and excess powdered potassium carbonate was stirred for 6 hr. The insoluble material was removed and the solution concentrated in vacuo. The residue was dissolved in ether and washed with 1N HCl. The acid washes were made basic with NaOH solution and the mixture was extracted with methylene chloride. The extracts were dried and concentrated in vacuo. The residue was converted to the hydrochloride salt with ethereal HCl to give a solid (75%, mp: 187°-188° C.). Calc'd for C18H24N2 O2.HCl: C, 64.18%; H, 7.48%; N, 8.32%. Found: C, 63.96%; H, 7.18%; N, 8.18%.

Workup

  1. customThe insoluble material was removed
  2. concentrationthe solution concentrated in vacuo
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with 1N HCl
  5. extractionthe mixture was extracted with methylene chloride
  6. customThe extracts were dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a00d2b32a3944f19e247d0d8132592d
Source dataset
uspto-grants-1998_07
Patent number
US05780470

Reaction notes

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