Benzo-1,3-dioxole-5-methylamine → HCID 12988935, compound

HRID 1354217Notes

Reaction equation

HRID 1354217 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+].[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[C:31]2[CH2:38][CH2:39][CH:40]1[CH2:45][CH2:44][C:43](=O)[CH2:42][CH2:41]1>ClCCl>[O:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH2:1][NH:11][CH:43]3[CH2:42][CH2:41][CH:40]([CH2:39][CH2:38][C:31]4[C:30]5[C:35](=[CH:36][CH:37]=[C:28]([O:27][CH3:26])[CH:29]=5)[N:34]=[CH:33][CH:32]=4)[CH2:45][CH2:44]3)=[CH:3][C:4]=2[O:5][CH2:6]1

Participants

5

Reactant 3

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 5049666Sodium triacetoxyborohydrideHCID 21104620HCID 21104620, compound

Product 1

HCID 12988935HCID 12988935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperonylamine (0.038 ml, 0.3 mmol) and sodium triacetoxyborohydride (0.05 g) were added to a solution of 4-[2-(6-methoxy-quinolin-4-yl)-ethyl]-cyclohexanone (0.05 g, 0.176 mmol) in dichloromethane (0.5 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 (EtOAc and then EtOAc:MeOH 9/1).

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 (EtOAc

Sources & evidence

ORD record
ord-13106611273a43e386869df139e252d1
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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