Benzyl Bromide → Benzenemethanamine, N-cyclohexyl-N-methyl-

HRID 620243Notes

Reaction equation

HRID 620243 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)CC(=O)C>[CH:3]1([N:2]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:1])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 7514N-MethylcyclohexylamineHCID 11430Potassium Carbonate

Product 1

HCID 9815624Benzenemethanamine, N-cyclohexyl-N-methyl-

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

The compound N-cyclohexyl-N-methylbenzylamine was synthesized by treatment of N-methylcyclohexylamine (1) [1.98 ml, 1.70 g, 0.015 moles] with benzyl bromide (2) [1.78 ml, 2.56 g, 0.015 moles] in the presence of potassium carbonate [2.28 g, 1.1 equivalents] in 4-methyl-2-pentanone (50 ml). The reaction mixture was heated under reflux overnight. After filtering the insoluble potassium salts, the filtrate was concentrated to dryness. The solid was dissolved in boiling 4-methyl-2-pentanone, treated with activated carbon, followed by hot filtration after which the purified compound precipitated upon cooling. It was collected by vacuum filtration. m.p. 173.5°-174.5° C. Proton NMR (CDCl3) reported downfield from TMS: 1.11-1.92 ppm multiplet 10 H cyclic alkyl ring, 2.65 ppm singlet 3 H N-methyl, 3.01-3.11 ppm multiplet 1 H tertiary proton, 4.19 ppm singlet 2 H benzylic --CH2 --, 7.44-7.80 ppm 5 H aromatic; C-13 nmr 131.12, 130.19, 129.08, 128.40, 63.11, 55.12, 35.23, 26.37, 25.06, 24.33. EI Mass Spec. M/e-(int) M+203 (28.4), M++1 204 (4.7), M++2 205 (0.2), 160 (70.7), 146 (10.6), 91 (100), 92 (7.1), 85 (5.6), 82 (5.2), 70 (17.6), 65 (24.7), 57 (5.7), 56 (5.3), 55 (15.0), 43 (3.6), 42 (32.3), 41 (20.1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationAfter filtering the insoluble potassium salts
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe solid was dissolved
  6. additiontreated with activated carbon
  7. filtrationfollowed by hot filtration after which the purified compound
  8. customprecipitated
  9. temperatureupon cooling
  10. filtrationIt was collected by vacuum filtration

Sources & evidence

ORD record
ord-2affabb3d799463bb248eddf09277706
Source dataset
uspto-grants-1989_04
Patent number
US04820737

Reaction notes

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