4-Methoxybenzylamine → 4-(4-Methoxy-benzylamino)-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]cyclohexanol

HRID 1354219Notes

Reaction equation

HRID 1354219 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:25][C:26]1([CH2:33][CH2:34][C:35]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([O:45][CH3:46])[CH:43]=3)[N:38]=[CH:37][N:36]=2)[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][CH:29]2[CH2:28][CH2:27][C:26]([CH2:33][CH2:34][C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[C:42]([O:45][CH3:46])[CH:43]=4)[N:38]=[CH:37][N:36]=3)([OH:25])[CH2:31][CH2:30]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 211046484-Hydroxy-4-[2-(6-methoxyquinazolin-4-yl)-ethyl]cyclohexanone

Product 1

HCID 211046284-(4-Methoxy-benzylamino)-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]cyclohexanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzylamine (0.026 ml, 0.24 mmol) and then sodium triacetoxyborohydride (0.08 g, 0.377 mmol) were added to a solution of 4-hydroxy-4-[2-(6-methoxyquinazolin-4-yl)-ethyl]cyclohexanone (0.06 g, 0.2 mmol) in dichloromethane (1 ml). The reaction mixture was stirred overnight and then filtered over Hydromatrix (wetted with an NaHCO3 solution, 2 ml) and subsequently washed with dichloromethane. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1 and then dichloromethane/MeOH 9/1 and 2% triethylamine).

Workup

  1. filtrationfiltered over Hydromatrix (
  2. washsubsequently washed with dichloromethane
  3. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  4. customThe residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1

Sources & evidence

ORD record
ord-b3b242b5777d42f78a899ab31919c96d
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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