HCID 17896794, compound → HCID 18180160, compound

HRID 1358935Notes

Reaction equation

HRID 1358935 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([CH:16]3[CH2:18][CH2:17]3)=O)[CH2:10][CH2:9]2)[CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:16]1([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:6]3[CH:7]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=3[O:19][CH3:20])[CH2:13][CH2:12]2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 17896794HCID 17896794, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18180160HCID 18180160, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(5-amino-2-methoxy-phenyl)-piperazin-1-yl]cyclopropyl methanone (D19) (1.6 mmol) in dry THF (10 ml) under argon was added LiAlH4 (240 mg, 6.4 mmol). The resulting mixture was heated to reflux for 12 hrs and cooled before quenching with water (0.25 ml), 10% aqueous NaOH (0.25 ml) and finally water (0.75 ml). Filtration through celite and concentration in vacuo afforded the title compound (D21) in 75% yield. Found MH+ 262.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 12 hrs
  3. temperaturecooled
  4. custombefore quenching with water (0.25 ml), 10% aqueous NaOH (0.25 ml) and finally water (0.75 ml)
  5. filtrationFiltration
  6. concentrationthrough celite and concentration in vacuo

Sources & evidence

ORD record
ord-6204c95100eb46269f10912b9debb30a
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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