Cyclohexylamine → HCID 22741972, compound

HRID 49894Notes

Reaction equation

HRID 49894 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][N:3]=1.[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])O.[Na+]>ClCCl>[CH:19]1([NH:25][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:4][N:3]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 516892Sodium BicarbonateHCID 19446091-Chloro-4-(4-pyridinylmethyl)phthalazine

Product 1

HCID 22741972HCID 22741972, compoundYield 0.56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 0.3 g (1.173 mmol) 1-chloro-4-(4-pyridylmethyl)phthalazine and 0.523 g (5.278 mmol) cyclohexylamine is stirred for 8 h at 115° C. The cooled reaction mixture is then distributed between dichloromethane and saturated aqueous sodium hydrogencarbonate solution. The organic solution washed with brine and dried over anhydrous sodium sulfate is evaporated and the residue purified on silica gel by flash chromatography using acetate/methanol (19:1). Title compound (with water content of 0.56%) is obtained after crystallization of the product-containing fractions from acetonitrile and drying under HV; m.p. 137-139° C.; ESI-MS: (M+H)+=319.

Workup

  1. customThe cooled reaction mixture
  2. washThe organic solution washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customis evaporated
  5. customthe residue purified on silica gel by flash chromatography

Sources & evidence

ORD record
ord-9fc24735bd184f0b815cb080e4fa531c
Source dataset
uspto-grants-2004_03
Patent number
US06710047B2

Reaction notes

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