Phenethylamine → 8-(Benzylmethylamino)octan-1-ol

HRID 2113099Notes

Reaction equation

HRID 2113099 reaction equation
[CH2:1]([CH2:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27]>CC(OC)(C)C.C(#N)C>[CH2:1]([CH2:8][NH:9][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 900121-Octanol, 8-chloro-

Product 1

HCID 688786308-(Benzylmethylamino)octan-1-olYield 96.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

A 2-L flask was charged with benzylmethylamine (270 g, 2.23 mol), sodium carbonate (157 g, 1.48 mol), sodium iodide (11.1 g, 0.074 mol), 8-chlorooctanol (122 g, 0.74 mol) and ACN (1000 mL) and the resulting suspension was stirred at 80° C. for 20-30 hours. The reaction mixture was then concentrated to a volume of about 500 mL and water (600 mL) and MTBE (1000 mL) were added. The MTBE layer was then separated and washed with water (500 mL). The MTBE solution was concentrated under vacuum and the resulting oil was then further concentrated by distillation under high vacuum to remove excess benzylmethylamine. N-methyl-2-pyrrolidone (300 mL) was then added to the remaining oil and this solution concentrated by distillation under high vacuum to provide an oil. The oil was dissolved in MTBE (1000 mL) and the resulting solution was washed with water (2×500 mL), brine (500 mL), dried with sodium sulfate (100 g), filtered and concentrated by distillation to afford the title compound as an oil (178 g, 96% yield, >95% purity).

Workup

  1. concentrationThe reaction mixture was then concentrated to a volume of about 500 mL and water (600 mL) and MTBE (1000 mL)
  2. additionwere added
  3. customThe MTBE layer was then separated
  4. washwashed with water (500 mL)
  5. concentrationThe MTBE solution was concentrated under vacuum
  6. concentrationthe resulting oil was then further concentrated by distillation under high vacuum
  7. customto remove excess benzylmethylamine
  8. additionN-methyl-2-pyrrolidone (300 mL) was then added to the remaining oil
  9. concentrationthis solution concentrated by distillation under high vacuum
  10. customto provide an oil
  11. washthe resulting solution was washed with water (2×500 mL), brine (500 mL)
  12. dry with materialdried with sodium sulfate (100 g)
  13. filtrationfiltered
  14. concentrationconcentrated by distillation

Sources & evidence

ORD record
ord-de841d7090514f18a8ab96166ad0a3d5
Source dataset
uspto-grants-2009_04
Patent number
US07524880B2

Reaction notes

Loading…