Methylamine → Ammonia

HRID 2105614Notes

Reaction equation

HRID 2105614 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=4)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.CN.[BH4-].[Na+].ClCCl>CO>[NH3:11].[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH:24]([OH:26])[CH3:25])=[CH:20][CH:19]=4)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 57808205HCID 57808205, compound

Product 2

HCID 222AmmoniaHCID 57807979HCID 57807979, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To the suspension of 1-{4-[2-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)-pyridin-4-yl]-phenyl}-ethanone (Example 7, 0.19 g, 0.55 mmol) in 2 mL of MeOH was added a solution of methylamine in MeOH (Aldrich Chemical Company) (2N, 0.55 mL, 1.1 mmol). The reaction was stirred at room temperature under nitrogen overnight. NaBH4 (Aldrich Chemical Company) (25 mg, 0.66 mmol) was then added to the reaction and it was stirred for another 5 hrs. The solvent was dichloromethane:2N NH3 in MeOH) to give the title compound as an off-white foam. MS (ESI, pos. ion) m/z: 349 (M+1). Mp: 55.9-61.5° C.

Workup

  1. stirringwas stirred for another 5 hrs

Sources & evidence

ORD record
ord-fa802db683044648b592768d9ae84919
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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