Dimethylamine → Benzenemethanamine, 4-amino-N,N-dimethyl-

HRID 1442641Notes

Reaction equation

HRID 1442641 reaction equation
CNC.[CH3:4][N:5]([CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1.[BH4-].[Na+]>C(O)C>[CH3:16][N:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:4]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 278498N,N-Dimethyl-4-nitrobenzylamineHCID 4311764Sodium borohydride

Product 1

HCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Using the procedure of Example 1, dimethylamine Compound 4a1 was used in place of Compound 1n2 and carried forward to prepare dimethyl-(4-nitrobenzyl)-amine Compound 4a2. Stannous chloride (28.1 g, 148 mmol) was added to a solution of Compound 4a2 (5.33 g, 29.6 mmol) in ethanol (200 mL) and heated to 60° C. Sodium borohydride (0.560 g, 14.8 mmol) in ethanol (80 mL) was added dropwise. Two hrs later the reaction mixture was added to ice water. The slurry was filtered through Celite 545 and the filtrate cake rinsed with ether. The collected liquors were brought to pH 11 with 1N NaOH and extracted with ether. The combined organic layers were washed with water, dried over MgSO4 and filtered. The dried organic solution was then reduced in vacuo to provide 4-dimethylaminomethyl-phenylamine Compound 4a which was used in the next step without further purification. MS 207 (MH+).

Workup

  1. filtrationThe slurry was filtered through Celite 545
  2. washthe filtrate cake rinsed with ether
  3. extractionextracted with ether
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b22871bb28ff4c928e5914b334715dec
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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