Benzylamine → Benzyl-[4-(6-methoxy-quinazolin-4-yloxymethyl)-cyclohexyl]-amine

HRID 1354223Notes

Reaction equation

HRID 1354223 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][N:19]=[C:18]2[O:25][CH2:26][CH:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1>CO>[CH2:1]([NH:8][CH:30]1[CH2:29][CH2:28][CH:27]([CH2:26][O:25][C:18]2[C:17]3[C:22](=[CH:23][CH:24]=[C:15]([O:14][CH3:13])[CH:16]=3)[N:21]=[CH:20][N:19]=2)[CH2:32][CH2:31]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 211046314-(6-Methoxy-quinazolin-4-yloxymethyl)-cyclohexanone

Product 1

HCID 21104686Benzyl-[4-(6-methoxy-quinazolin-4-yloxymethyl)-cyclohexyl]-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzylamine (1.08 ml, 10 mmol) and sodium cyanoborohydride (2.2 g, 11 mmol) were added to a solution of 4-(6-methoxy-quinazolin-4-yloxymethyl)-cyclohexanone (2.87 g, 10 mmol) in methanol (50 ml). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated and the residue was dissolved in saturated potassium carbonate solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate (2×50 ml), and the combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by column chromatography on silica gel (EtOAc and then EtOAc/MeOH 9/1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in saturated potassium carbonate solution
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  4. dry with materialthe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (EtOAc

Sources & evidence

ORD record
ord-7afb3496faf44b7496e83e3307b9fb2a
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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