N-Methylbenzylamine → 8-(N-Benzyl-N-methylamino)octan-1-ol

HRID 2113097Notes

Reaction equation

HRID 2113097 reaction equation
[CH2:1]([NH:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25]>C(#N)C>[CH2:1]([N:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 1626071-Octanol, 8-bromo-

Product 1

HCID 166621538-(N-Benzyl-N-methylamino)octan-1-olYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 250 mL flask was charged N-benzyl-N-methylamine (24.3 g, 200 mmol), potassium carbonate (28 g, 200 mmol), 8-bromooctan-1-ol (14 g, 67 mmol) and ACN (150 mL). This reaction mixture was stirred at 35° C. to 40° C. for 5 hours. The solid material was then filtered and the filtrate was distilled to an oil under high vacuum to remove excess N-benzyl-N-methylamine. The residue was dissolved in MTBE (150 mL) and washed with 15% ammonium chloride solution (2×100 mL), brine (100 mL), dried with 20 g of sodium sulfate, filtered and distilled under vacuum to give the title intermediate as an oil (13.2 g, 79% yield).

Workup

  1. filtrationThe solid material was then filtered
  2. distillationthe filtrate was distilled to an oil under high vacuum
  3. customto remove excess N-benzyl-N-methylamine
  4. dissolutionThe residue was dissolved in MTBE (150 mL)
  5. washwashed with 15% ammonium chloride solution (2×100 mL), brine (100 mL)
  6. dry with materialdried with 20 g of sodium sulfate
  7. filtrationfiltered
  8. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-4f88a82e8da14466a1800067a0b798a3
Source dataset
uspto-grants-2009_04
Patent number
US07524880B2

Reaction notes

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