Butylamine → Ethyl 2-{4-[(butylamino)methyl]-2-methylphenoxy}-2-methylpropanoate

HRID 1269594Notes

Reaction equation

HRID 1269594 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:18])[CH:4]=1)=O.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:19]([NH:23][CH2:1][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:18])[CH:4]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18448413Ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate

Product 1

HCID 18448412Ethyl 2-{4-[(butylamino)methyl]-2-methylphenoxy}-2-methylpropanoateYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate (0.56 g, 2.25 mmol) in anhydrous CH2Cl2 (10 mL) was added n-butylamine (0.33 mL, 3.38 mmol). After stirring for 90 mins under nitrogen at room temperature, sodium triacetoxyborohydride (0.668 g, 3.15 mmol) was added and stirring continued for 18 h. The reaction was quenched by cautious addition of sat. sodium carbonate aq. (20 mL) and then extracted CH2Cl2 (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 (0.48 g).

Workup

  1. stirringstirring
  2. waitcontinued for 18 h
  3. customThe reaction was quenched by cautious addition of sat. sodium carbonate aq. (20 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-5744e60be78641018a9f121f1c3cbf81
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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