Phenethylamine → N-Cyclohexyl-p-ethoxyaniline

HRID 2043876Notes

Reaction equation

HRID 2043876 reaction equation
C(N)C[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[BH3-]C#[N:19].[Na+].C1C[O:24][CH2:23][CH2:22]1.CO>>[CH:10]1([NH:19][C:3]2[CH:4]=[CH:5][C:6]([O:24][CH2:23][CH3:22])=[CH:7][CH:8]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 4

HCID 1001PhenethylamineHCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 69759N-Cyclohexyl-p-ethoxyaniline

Procedure

Phenethylamine (121 mg, 1.0 mmol) in a 2:1 mixture of THF-MeOH (2 mL) was added cyclohexanone (98 mg, 1.0 mmol) and molecular sieves (4A, 80 mg). The reaction mixture was shaken for 1 h before NaBH3CN (126 mg, 2.0 mmol) was added. The reaction mixture was shaken for 24 h before it was filtered and the filtrate was concentrated in vacuo to give the intermediate cyclohexyl phenetylamine.

Workup

  1. additionwas added
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-649ca8f7963c4ad6a6d5e120e7568a72
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

Loading…