Methylamine → HCID 178484783, compound

HRID 1884513Notes

Reaction equation

HRID 1884513 reaction equation
[CH3:1][NH2:2].[C:3]1([CH:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1>[CH3:1][NH:2][C@H:12]1[CH2:13][CH2:14][C@H:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 786054-Phenylcyclohexanone

Product 1

HCID 178484783HCID 178484783, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methylamine (5.7 mL of a 2.0 M in THF, 11.4 mmol) was added to a solution of 4-phenylcyclohexanone 1 (2.0 g, 11 mmol) in anhydrous THF (30 mL), and the mixture was stirred at room temperature for 4 hours. BH3—SMe2 1.6 mL, 16 mmol) was added, and stirring was continued overnight. After quenching the reaction with MeOH, the solvents were removed under reduced pressure. The crude solid was dissolved in MeOH (10 mL), HCl (15 mL of a 1.0 M solution in Et2O, 15 mmol) was added, and the mixture concentrated under reduced pressure. Purification by flash chromatography (silica, 9:1:0.1 CH2Cl2: MeOH:NH4OH) gave trans-1-(methylamino)-4-phenylcyclohexane 6 (0.80 g, 39%) as a white solid: 1H NMR (300 MHz, CD3 OD) δ 7.27-7.11 (m, 5H), 2.64 m, 1H), 2.51 (obs m, 1H), 2.48 (s, 3H), 2.47 (s, 3H), 2.11 (br d, J=11 Hz, 2H), 1.93 (br d, J=11 Hz, 2H), 1.59 (dddd, J=11, 11, 2, 2 Hz, 2H), 1.42 (dddd, J=11, 11, 2, 2 Hz, 2H).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customAfter quenching
  4. customthe reaction with MeOH
  5. customthe solvents were removed under reduced pressure
  6. dissolutionThe crude solid was dissolved in MeOH (10 mL)
  7. additionHCl (15 mL of a 1.0 M solution in Et2O, 15 mmol) was added
  8. concentrationthe mixture concentrated under reduced pressure
  9. customPurification by flash chromatography (silica, 9:1:0.1 CH2Cl2: MeOH:NH4OH)

Sources & evidence

ORD record
ord-dc7238c74ba64692b00d34db4cd5d4b1
Source dataset
uspto-grants-2004_07
Patent number
US06765022B2

Reaction notes

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