Butylamine → Methyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

HRID 1269595Notes

Reaction equation

HRID 1269595 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12]C)=[O:10])=[C:5]([CH3:16])[CH:4]=1)=O.[CH2:17]([NH2:21])[CH2:18][CH2:19][CH3:20].[BH4-].[Na+]>CO>[CH2:17]([NH:21][CH2:1][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH3:16])[CH:4]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 4311764Sodium borohydrideHCID 58622891Ethyl (4-formyl-2-methylphenoxy)acetate

Product 1

HCID 58622898Methyl {4-[(butylamino)methyl]-2-methylphenoxy}acetateYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (4-formyl-2-methylphenoxy)acetate (0.65 g, 2.93 mmol) in anyhdrous methanol (12 mL) under nitrogen was added n-butylamine (0.3 mL, 3.07 mmol) and the resultant mixture stirred for 18 h at room temperature, prior to portion wise addition of sodium borohydride (0.144 g, 3.8 mmol). After 30 minutes stirring at room temperature the reaction was quenched by cautious addition of sat. sodium bicarbonate aq. and then extracted into ethyl acetate (2×40 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo to afford the title compound as a pale yellow oil (0.65 g).

Workup

  1. customwas quenched by cautious addition of sat. sodium bicarbonate aq.
  2. extractionextracted into ethyl acetate (2×40 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-090f2d890ff540a680fbf234dbedced4
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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