Sodium Hydroxide → Cyclopropyl-[4-(6-methoxy-indan-1-yl)-piperazin-1-yl]-methanone

HRID 1956154Notes

Reaction equation

HRID 1956154 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=O)=[CH:5][CH:4]=1.[CH:13]1([C:16]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:17])[CH2:15][CH2:14]1.[BH4-].[Na+].[OH-].[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:13]1([C:16]([N:18]2[CH2:23][CH2:22][N:21]([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)[CH2:20][CH2:19]2)=[O:17])[CH2:14][CH2:15]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 3340366-Methoxy-1-IndanoneHCID 20642351-(Cyclopropylcarbonyl)piperazineHCID 4311764Sodium borohydride2×

Product 1

HCID 22375366Cyclopropyl-[4-(6-methoxy-indan-1-yl)-piperazin-1-yl]-methanone

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalyst2×HCID 702EthanolSolvent

Procedure

An intimate mixture of 6-methoxy-1-indanone (1.6 g, 10 mmol), 1-cyclopropanecarbonylpiperazine (1.5 g, 10 mmol) and titanium(IV) isopropoxide (4 mL, 12 mmol) was heated on the steam bath for 10 minutes. Additional titanium isopropoxide (1 mL, 3 mmol) was added and the mixture stirred for 20 hr. The material was dissolved in ethanol and sodium borohydride added (0.9 g, 22 mmol). After stirring for 1 hr the solution was heated to reflux and more sodium borohydride (0.9 g, 22 mmol) added. When solution had occurred 15% NaOH solution (50 mL) was added. The insoluble material was removed and discarded. The solution was concentrated in vacuo and the residue mixed with ether. The mixture was washed with water and 1N HCl solution. The acid washes were made basic and the mixture was extracted with ether to give the product as an oil which was converted to the fumarate salt and crystallized from acetone to give the salt (1.8 g).

Workup

  1. temperaturewas heated on the steam bath for 10 minutes
  2. stirringAfter stirring for 1 hr the solution
  3. temperaturewas heated
  4. temperatureto reflux
  5. additionwas added
  6. customThe insoluble material was removed
  7. concentrationThe solution was concentrated in vacuo
  8. additionthe residue mixed with ether
  9. washThe mixture was washed with water and 1N HCl solution
  10. extractionthe mixture was extracted with ether

Sources & evidence

ORD record
ord-ea58ff6eb29148ba89f4b595a4f08e53
Source dataset
uspto-grants-1998_07
Patent number
US05780470

Reaction notes

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