N-Methylbenzeneethanamine → 9-(Methyl-phenethyl-amino)-nonanoic acid methyl ester

HRID 1799664Notes

Reaction equation

HRID 1799664 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=O.[CH3:14][NH:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+]>CO.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:15]([CH3:14])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11503N-MethylbenzeneethanamineHCID 74732Methyl 9-oxononanoateHCID 4311764Sodium borohydride

Product 1

HCID 668742049-(Methyl-phenethyl-amino)-nonanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 9-oxononanoic acid methyl ester (J. Org. Chem. 2007, 72, 9471; 303 mg, 1.63 mmol) and N-methyl-2-phenylethylamine (220 mg, 1.63 mmol) in methanol (10 mL) was added concentrated sulfuric acid (5 drops) at room temperature, then after 40 h the solution was heated at reflux for 2 h. After cooling sodium borohydride (123 mg, 3.25 mmol) was added, then after 1 h the reaction mixture was partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate, filtered, and evaporated to afford 9-(methyl-phenethyl-amino)-nonanoic acid methyl ester as a light yellow liquid.

Workup

  1. temperatureafter 40 h the solution was heated
  2. temperatureat reflux for 2 h
  3. additionwas added
  4. customafter 1 h the reaction mixture was partitioned between water and dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5cd786a82e3b4f79af6a489c21677c4c
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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