Benzo-1,3-dioxole-5-methylamine → 4-[(Benzo[1.3]dioxol-5-ylmethyl)-amino]-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol

HRID 1354208Notes

Reaction equation

HRID 1354208 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:26][C:27]1([CH2:34][CH2:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[C:43]([O:46][CH3:47])[CH:44]=3)[N:39]=[CH:38][N:37]=2)[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1>ClCCl>[O:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH2:1][NH:11][CH:30]3[CH2:29][CH2:28][C:27]([CH2:34][CH2:35][C:36]4[C:45]5[C:40](=[CH:41][CH:42]=[C:43]([O:46][CH3:47])[CH:44]=5)[N:39]=[CH:38][N:37]=4)([OH:26])[CH2:32][CH2:31]3)=[CH:3][C:4]=2[O:5][CH2:6]1

Participants

5

Reactant 3

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 5049666Sodium triacetoxyborohydrideHCID 211046484-Hydroxy-4-[2-(6-methoxyquinazolin-4-yl)-ethyl]cyclohexanone

Product 1

HCID 211046414-[(Benzo[1.3]dioxol-5-ylmethyl)-amino]-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperonylamine (0.030 ml, 0.24 mmol) and sodium triacetoxyborohydride (0.08 g, 0.377 mmol) were added to a solution of 4-hydroxy-4-[2-(6-methoxy-quinazolin-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

Sources & evidence

ORD record
ord-2c8e4680a5064993bc11aba618bda5c5
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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