Water → 1-(3-Methoxyphenyl)cyclohexan-1-amine
Reaction equation
[N:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([C:4]2([NH2:1])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:15]=[CH:14][CH:13]=1Participants
Procedure
To a solution of 1-(1-azidocyclohexyl)-3-(methyloxy)benzene (D315) (2.78 g, 12.0 mmol, 1 equiv) in THF (20 ml) at room temperature was added LiAlH4 (1M in THF, 36 ml, 36 mmol, 3 equiv) and the resulting mixture was stirred at this temperature for 4 h. The mixture was then carefully quenched with a 1N aqueous NaOH solution (6 ml, 60 mmol, 1 equiv) then H2O. The mixture was filtered through a pad of celite then acidified with a 2N aqueous HCl solution (50 ml). The two layers were separated and the pH of the aqueous phase adjusted to 9 using a 2N aqueous NaOH solution. The aqueous phase was extracted three times with Et2O and the combined organic phase were dried over MgSO4 then concentrated in vacuo to give {1-[3-(methyloxy)phenyl]cyclohexyl}amine (F41) (1.55 g, 63%) as a clear oil which was used in the next step without further purification. [M+H]+=189.0, RT=1.90 min.
Workup
- filtrationThe mixture was filtered through a pad of celite
- customThe two layers were separated
- extractionThe aqueous phase was extracted three times with Et2O
- dry with materialthe combined organic phase were dried over MgSO4
- concentrationthen concentrated in vacuo
Sources & evidence
- ORD record
- ord-470a17aad2384d3086f478e5ba41633c
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253198B2
Reaction notes
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